Pyrrole

Formula: C₄H₅N
Molecular weight: 67.0892
IUPAC Standard InChI: InChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H
IUPAC Standard InChIKey: KAESVJOAVNADME-UHFFFAOYSA-N
CAS Registry Number: 109-97-7
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Other names: 1H-Pyrrole; Azole; Divinylenimine; Imidole; Monopyrrole; Pyrrol; 1-Aza-2,4-cyclopentadiene; Divinyleneimine; Parzate; NSC 62777
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	34.23	kcal/mol	N/A	Zaheeruddin and Lodhi, 1991	Value computed using Δ_fH_liquid° value of 98.0 kj/mol from Zaheeruddin and Lodhi, 1991 and Δ_vapH° value of 45.2 kj/mol from Scott, Berg, et al., 1967.; DRB
Δ_fH°_gas	25.88 ± 0.12	kcal/mol	Ccb	Scott, Berg, et al., 1967	ALS

Condensed phase thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid			Ccb	Zaheeruddin and Lodhi, 1991	uncertain value: 23.43 kcal/mol; ALS
Δ_fH°_liquid	15.1 ± 0.1	kcal/mol	Ccb	Scott, Berg, et al., 1967	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid			Ccb	Zaheeruddin and Lodhi, 1991	uncertain value: -570.425 kcal/mol; ALS
Δ_cH°_liquid	-562.07 ± 0.08	kcal/mol	Ccb	Scott, Berg, et al., 1967	ALS
Δ_cH°_liquid	-561.6	kcal/mol	Ccb	Zimmerman and Geisenfelder, 1961	ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	37.390	cal/mol*K	N/A	Scott, Berg, et al., 1967	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
30.531	298.15	Scott, Berg, et al., 1967	T = 11 to 365 K.; DH

Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
T_boil	403. ± 1.	K	AVG	N/A	Average of 15 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	250.15	K	N/A	Rosso and Carbonnel, 1973	Uncertainty assigned by TRC = 0.6 K; TRC
T_fus	254.7	K	N/A	Timmermans and Hennaut-Roland, 1955	Uncertainty assigned by TRC = 0.5 K; TRC
T_fus	249.7	K	N/A	Anonymous, 1942	Uncertainty assigned by TRC = 0.2 K; TRC
T_fus	238.8	K	N/A	Milazzo, 1941	Uncertainty assigned by TRC = 0.4 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_triple	249.7300	K	N/A	Scott, Berg, et al., 1967, 2	Uncertainty assigned by TRC = 0.07 K; by extrapolation of 1/f to zero; TRC
T_triple	249.74	K	N/A	Helm, Lanum, et al., 1958	Uncertainty assigned by TRC = 0.03 K; measured in calorimeter at U.S. Bur. Mines, Bartlesville, OK; TRC
T_triple	249.74	K	N/A	McCullough and Waddington, 1957	Uncertainty assigned by TRC = 0.06 K; IPTS-48, from freezing curve; TRC
T_triple	249.74	K	N/A	McCullough and Waddington, 1957	Uncertainty assigned by TRC = 0.06 K; IPTS-48, from heating curve; TRC
Quantity	Value	Units	Method	Reference	Comment
T_c	639.8	K	N/A	Majer and Svoboda, 1985
T_c	639.7	K	N/A	Cheng, McCoubrey, et al., 1962	Uncertainty assigned by TRC = 1.5 K; extrapolated to zero time to correct for decomposition cal. vs NPL thermometer.; TRC
T_c	625.15	K	N/A	Glaser and Ruland, 1957	Uncertainty assigned by TRC = 2. K; TRC
Quantity	Value	Units	Method	Reference	Comment
P_c	56.000	atm	N/A	Glaser and Ruland, 1957	Uncertainty assigned by TRC = 3.0000 atm; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	10. ± 1.	kcal/mol	AVG	N/A	Average of 6 values; Individual data points

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
9.261	403.	N/A	Majer and Svoboda, 1985
10.2	300.	N/A	Kimizuka and Szydlowski, 1992	Based on data from 285. to 329. K.; AC
10.2	353.	A,EB,IP	Stephenson and Malanowski, 1987	Based on data from 338. to 440. K. See also Osborn and Douslin, 1968 and Scott, Berg, et al., 1967.; AC
10.0	328.	I	Eon, Pommier, et al., 1971	Based on data from 313. to 373. K.; AC
10.0	348.	N/A	Stull, 1947	Based on data from 333. to 373. K.; AC

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
T_r = reduced temperature (T / T_c)

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Temperature (K)	A (kcal/mol)	β	T_c (K)	Reference	Comment
362. to 403.	15.0	0.2964	639.8	Majer and Svoboda, 1985

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)

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Temperature (K)	A	B	C	Reference	Comment
333.4 to 373.5	5.31520	2074.447	-9.186	Eon, Pommier, et al., 1971	Coefficents calculated by NIST from author's data.
338.82 to 439.26	4.42194	1506.877	-62.155	Osborn and Douslin, 1968

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Reference	Comment
1.8900	249.74	Scott, Berg, et al., 1967	DH
1.89	249.7	Domalski and Hearing, 1996	AC

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
7.567	249.74	Scott, Berg, et al., 1967	DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Reaction thermochemistry data

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Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

+ = Pyrrole

By formula: C₄H₄N^- + H⁺ = C₄H₅N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	359.54 ± 0.25	kcal/mol	D-EA	Gianola, Ichino, et al., 2004	gas phase; B
Δ_rH°	358.6 ± 2.2	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Δ_rH°	359.6 ± 2.9	kcal/mol	G+TS	Cumming and Kebarle, 1978	gas phase; B
Δ_rH°	358.6 ± 5.0	kcal/mol	EIAE	Muftakhov, Vasil'ev, et al., 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	350.9 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Δ_rG°	351.8 ± 2.0	kcal/mol	IMRE	Cumming and Kebarle, 1978	gas phase; B

CN^- + Pyrrole = (CN^- • Pyrrole )

By formula: CN^- + C₄H₅N = (CN^- • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	23.4 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988	gas phase; B,M
Δ_rH°	19.5 ± 3.5	kcal/mol	IMRE	Larson and McMahon, 1987	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	27.1	cal/mol*K	PHPMS	Meot-ner, 1988	gas phase; M
Δ_rS°	23.8	cal/mol*K	N/A	Larson and McMahon, 1987	gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	15.3 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988	gas phase; B
Δ_rG°	12.3 ± 2.3	kcal/mol	IMRE	Larson and McMahon, 1987	gas phase; B,M

+ Pyrrole = ( • Pyrrole )

By formula: F^- + C₄H₅N = (F^- • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	34.2 ± 2.0	kcal/mol	IMRE	Larson and McMahon, 1983	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	25.5	cal/mol*K	N/A	Larson and McMahon, 1983	gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	26.6 ± 2.0	kcal/mol	IMRE	Larson and McMahon, 1983	gas phase; B,M

+ Pyrrole = ( • Pyrrole )

By formula: Cl^- + C₄H₅N = (Cl^- • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	18.8 ± 2.0	kcal/mol	IMRE	Larson and McMahon, 1984	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	11.8 ± 2.0	kcal/mol	IMRE	Larson and McMahon, 1984	gas phase; B
Δ_rG°	14.00	kcal/mol	TDEq	French, Ikuta, et al., 1982	gas phase; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
11.6	421.	PHPMS	French, Ikuta, et al., 1982	gas phase; M

HS^- + Pyrrole = (HS^- • Pyrrole )

By formula: HS^- + C₄H₅N = (HS^- • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	23.0 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	24.4	cal/mol*K	PHPMS	Meot-ner, 1988	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	15.7 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988	gas phase; B

+ Pyrrole = ( • Pyrrole )

By formula: C₄H₄N^- + C₄H₅N = (C₄H₄N^- • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	26.5 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988, 2	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	35.2	cal/mol*K	PHPMS	Meot-ner, 1988, 2	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	16.3 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988, 2	gas phase; B

+ Pyrrole = ( • Pyrrole )

By formula: C₂H₃O₂^- + C₄H₅N = (C₂H₃O₂^- • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	24.0 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	25.1	cal/mol*K	PHPMS	Meot-ner, 1988	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	16.5 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988	gas phase; B

(C₄H₅N⁺ • Pyrrole ) + Pyrrole = (C₄H₅N⁺ • 2 Pyrrole )

By formula: (C₄H₅N⁺ • C₄H₅N) + C₄H₅N = (C₄H₅N⁺ • 2C₄H₅N)

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	13.8	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	29.2	cal/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

C₄H₅N⁺ + Pyrrole = (C₄H₅N⁺ • Pyrrole )

By formula: C₄H₅N⁺ + C₄H₅N = (C₄H₅N⁺ • C₄H₅N)

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	16.5	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	20.3	cal/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

(C₄H₆N⁺ • Pyrrole ) + Pyrrole = (C₄H₆N⁺ • 2 Pyrrole )

By formula: (C₄H₆N⁺ • C₄H₅N) + C₄H₅N = (C₄H₆N⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	12.3	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	30.4	cal/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (C₄H₄N^- • C₄H₅N) + C₄H₅N = (C₄H₄N^- • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	17.1	kcal/mol	PHPMS	Meot-ner, 1988, 2	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	31.2	cal/mol*K	PHPMS	Meot-ner, 1988, 2	gas phase; M

C₄H₆N⁺ + Pyrrole = (C₄H₆N⁺ • Pyrrole )

By formula: C₄H₆N⁺ + C₄H₅N = (C₄H₆N⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	16.8	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	24.7	cal/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (C₂H₃O₂^- • C₄H₅N) + C₄H₅N = (C₂H₃O₂^- • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	17.9	kcal/mol	PHPMS	Meot-ner, 1988	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	24.2	cal/mol*K	PHPMS	Meot-ner, 1988	gas phase; M

CH₆N⁺ + Pyrrole = (CH₆N⁺ • Pyrrole )

By formula: CH₆N⁺ + C₄H₅N = (CH₆N⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	18.6	kcal/mol	PHPMS	Deakyne and Meot-Ner (Mautner), 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	21.0	cal/mol*K	PHPMS	Deakyne and Meot-Ner (Mautner), 1985	gas phase; M

+ Pyrrole = ( • Pyrrole )

By formula: C₆H₁₁NO₃ + C₄H₅N = (C₆H₁₁NO₃ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	24.0	kcal/mol	PHPMS	Meot-Ner (Mautner), 1988	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	32.1	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1988	gas phase; M

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (Fe⁺ • C₄H₅N) + C₄H₅N = (Fe⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	41.6	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (Cr⁺ • C₄H₅N) + C₄H₅N = (Cr⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	34.9	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (Mn⁺ • C₄H₅N) + C₄H₅N = (Mn⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	27.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (Ni⁺ • C₄H₅N) + C₄H₅N = (Ni⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	47.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (Co⁺ • C₄H₅N) + C₄H₅N = (Co⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	46.4	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (Cu⁺ • C₄H₅N) + C₄H₅N = (Cu⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	44.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Li⁺ + C₄H₅N = (Li⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	42.3 ± 4.0	kcal/mol	CIDT	Huang and Rodgers, 2002	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Na⁺ + C₄H₅N = (Na⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	24.3 ± 1.1	kcal/mol	CIDT	Huang and Rodgers, 2002	RCD

+ Pyrrole = ( • Pyrrole )

By formula: K⁺ + C₄H₅N = (K⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	20.0 ± 1.0	kcal/mol	CIDT	Huang and Rodgers, 2002	RCD

+ Pyrrole = ( • Pyrrole )

By formula: V⁺ + C₄H₅N = (V⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	>41.	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Ni⁺ + C₄H₅N = (Ni⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	>68.	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: W⁺ + C₄H₅N = (W⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	>50.	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Co⁺ + C₄H₅N = (Co⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	>66.	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Mo⁺ + C₄H₅N = (Mo⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	>69.	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Fe⁺ + C₄H₅N = (Fe⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	54.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Cr⁺ + C₄H₅N = (Cr⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	42.5	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Mn⁺ + C₄H₅N = (Mn⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	42.3	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Mg⁺ + C₄H₅N = (Mg⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	44.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Al⁺ + C₄H₅N = (Al⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	44.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Cu⁺ + C₄H₅N = (Cu⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	59.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References, Notes

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	8.207 ± 0.005	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	209.2	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	201.7	kcal/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.02	PE	Klasinc, Sabljic, et al., 1982	LBLHLM
8.02	PE	Galasso, Klasinc, et al., 1981	LLK
8.21	PE	Willett and Baer, 1980	LLK
8.4 ± 0.1	CEMS	Tedder and Vidaud, 1980	LLK
8.207 ± 0.003	PI	Cooper, Williamson, et al., 1980	LLK
8.208 ± 0.005	PI	Williamson, Compton, et al., 1979	LLK
~8.1	EI	Van Veen, 1976	LLK
8.22 ± 0.05	EI	Thorstad and Undheim, 1974	LLK
8.40 ± 0.05	EI	Linda, Marino, et al., 1971	LLK
8.209	PE	Derrick, Asbrink, et al., 1971	LLK
8.209	S	Derrick, Asbrink, et al., 1971	LLK
8.20 ± 0.01	PI	Potapov and Yuzhakova, 1970	RDSH
8.20 ± 0.01	PI	Potapov and Bazhenov, 1970	RDSH
8.20 ± 0.01	PI	Watanabe, Nakayama, et al., 1962	RDSH
8.23	PE	Cradock, Findlay, et al., 1973	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
CH₂N⁺	12.40	?	PI	Willett and Baer, 1980	LLK
CH₂N⁺	12.1 ± 0.2	C₃H₃	CEMS	Tedder and Vidaud, 1980	LLK
C₂H₃⁺	13.60	?	PI	Willett and Baer, 1980	LLK
C₂H₃N⁺	11.75	C₂H₂	EI	Sakurai and Jennings, 1981	LLK
C₂H₃N⁺	11.75	?	PI	Willett and Baer, 1980	LLK
C₃H₂N⁺	12.50	?	PI	Willett and Baer, 1980	LLK
C₃H₃⁺	12.60	?	PI	Willett and Baer, 1980	LLK
C₃H₄⁺	12.00	?	PI	Willett and Baer, 1980	LLK
C₃H₄⁺	12.5 ± 0.2	CHN	CEMS	Tedder and Vidaud, 1980	LLK
C₄H₄N⁺	12.85	H	PI	Willett and Baer, 1980	LLK

De-protonation reactions

+ = Pyrrole

By formula: C₄H₄N^- + H⁺ = C₄H₅N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	359.54 ± 0.25	kcal/mol	D-EA	Gianola, Ichino, et al., 2004	gas phase; B
Δ_rH°	358.6 ± 2.2	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Δ_rH°	359.6 ± 2.9	kcal/mol	G+TS	Cumming and Kebarle, 1978	gas phase; B
Δ_rH°	358.6 ± 5.0	kcal/mol	EIAE	Muftakhov, Vasil'ev, et al., 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	350.9 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Δ_rG°	351.8 ± 2.0	kcal/mol	IMRE	Cumming and Kebarle, 1978	gas phase; B

Ion clustering data

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Data compiled as indicated in comments:
RCD - Robert C. Dunbar
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

+ Pyrrole = ( • Pyrrole )

By formula: Al⁺ + C₄H₅N = (Al⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	44.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

CH₆N⁺ + Pyrrole = (CH₆N⁺ • Pyrrole )

By formula: CH₆N⁺ + C₄H₅N = (CH₆N⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	18.6	kcal/mol	PHPMS	Deakyne and Meot-Ner (Mautner), 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	21.0	cal/mol*K	PHPMS	Deakyne and Meot-Ner (Mautner), 1985	gas phase; M

CN^- + Pyrrole = (CN^- • Pyrrole )

By formula: CN^- + C₄H₅N = (CN^- • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	23.4 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988	gas phase; B,M
Δ_rH°	19.5 ± 3.5	kcal/mol	IMRE	Larson and McMahon, 1987	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	27.1	cal/mol*K	PHPMS	Meot-ner, 1988	gas phase; M
Δ_rS°	23.8	cal/mol*K	N/A	Larson and McMahon, 1987	gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	15.3 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988	gas phase; B
Δ_rG°	12.3 ± 2.3	kcal/mol	IMRE	Larson and McMahon, 1987	gas phase; B,M

+ Pyrrole = ( • Pyrrole )

By formula: C₂H₃O₂^- + C₄H₅N = (C₂H₃O₂^- • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	24.0 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	25.1	cal/mol*K	PHPMS	Meot-ner, 1988	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	16.5 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988	gas phase; B

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (C₂H₃O₂^- • C₄H₅N) + C₄H₅N = (C₂H₃O₂^- • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	17.9	kcal/mol	PHPMS	Meot-ner, 1988	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	24.2	cal/mol*K	PHPMS	Meot-ner, 1988	gas phase; M

+ Pyrrole = ( • Pyrrole )

By formula: C₄H₄N^- + C₄H₅N = (C₄H₄N^- • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	26.5 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988, 2	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	35.2	cal/mol*K	PHPMS	Meot-ner, 1988, 2	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	16.3 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988, 2	gas phase; B

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (C₄H₄N^- • C₄H₅N) + C₄H₅N = (C₄H₄N^- • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	17.1	kcal/mol	PHPMS	Meot-ner, 1988, 2	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	31.2	cal/mol*K	PHPMS	Meot-ner, 1988, 2	gas phase; M

C₄H₅N⁺ + Pyrrole = (C₄H₅N⁺ • Pyrrole )

By formula: C₄H₅N⁺ + C₄H₅N = (C₄H₅N⁺ • C₄H₅N)

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	16.5	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	20.3	cal/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

(C₄H₅N⁺ • Pyrrole ) + Pyrrole = (C₄H₅N⁺ • 2 Pyrrole )

By formula: (C₄H₅N⁺ • C₄H₅N) + C₄H₅N = (C₄H₅N⁺ • 2C₄H₅N)

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	13.8	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	29.2	cal/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

C₄H₆N⁺ + Pyrrole = (C₄H₆N⁺ • Pyrrole )

By formula: C₄H₆N⁺ + C₄H₅N = (C₄H₆N⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	16.8	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	24.7	cal/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

(C₄H₆N⁺ • Pyrrole ) + Pyrrole = (C₄H₆N⁺ • 2 Pyrrole )

By formula: (C₄H₆N⁺ • C₄H₅N) + C₄H₅N = (C₄H₆N⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	12.3	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	30.4	cal/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

+ Pyrrole = ( • Pyrrole )

By formula: Cl^- + C₄H₅N = (Cl^- • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	18.8 ± 2.0	kcal/mol	IMRE	Larson and McMahon, 1984	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	11.8 ± 2.0	kcal/mol	IMRE	Larson and McMahon, 1984	gas phase; B
Δ_rG°	14.00	kcal/mol	TDEq	French, Ikuta, et al., 1982	gas phase; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
11.6	421.	PHPMS	French, Ikuta, et al., 1982	gas phase; M

+ Pyrrole = ( • Pyrrole )

By formula: Co⁺ + C₄H₅N = (Co⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	>66.	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (Co⁺ • C₄H₅N) + C₄H₅N = (Co⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	46.4	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Cr⁺ + C₄H₅N = (Cr⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	42.5	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (Cr⁺ • C₄H₅N) + C₄H₅N = (Cr⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	34.9	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Cu⁺ + C₄H₅N = (Cu⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	59.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (Cu⁺ • C₄H₅N) + C₄H₅N = (Cu⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	44.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: F^- + C₄H₅N = (F^- • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	34.2 ± 2.0	kcal/mol	IMRE	Larson and McMahon, 1983	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	25.5	cal/mol*K	N/A	Larson and McMahon, 1983	gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	26.6 ± 2.0	kcal/mol	IMRE	Larson and McMahon, 1983	gas phase; B,M

+ Pyrrole = ( • Pyrrole )

By formula: Fe⁺ + C₄H₅N = (Fe⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	54.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (Fe⁺ • C₄H₅N) + C₄H₅N = (Fe⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	41.6	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

HS^- + Pyrrole = (HS^- • Pyrrole )

By formula: HS^- + C₄H₅N = (HS^- • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	23.0 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	24.4	cal/mol*K	PHPMS	Meot-ner, 1988	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	15.7 ± 1.0	kcal/mol	TDAs	Meot-ner, 1988	gas phase; B

+ Pyrrole = ( • Pyrrole )

By formula: K⁺ + C₄H₅N = (K⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	20.0 ± 1.0	kcal/mol	CIDT	Huang and Rodgers, 2002	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Li⁺ + C₄H₅N = (Li⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	42.3 ± 4.0	kcal/mol	CIDT	Huang and Rodgers, 2002	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Mg⁺ + C₄H₅N = (Mg⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	44.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Mn⁺ + C₄H₅N = (Mn⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	42.3	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (Mn⁺ • C₄H₅N) + C₄H₅N = (Mn⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	27.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Mo⁺ + C₄H₅N = (Mo⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	>69.	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Na⁺ + C₄H₅N = (Na⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	24.3 ± 1.1	kcal/mol	CIDT	Huang and Rodgers, 2002	RCD

+ Pyrrole = ( • Pyrrole )

By formula: Ni⁺ + C₄H₅N = (Ni⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	>68.	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

( • Pyrrole ) + Pyrrole = ( • 2 Pyrrole )

By formula: (Ni⁺ • C₄H₅N) + C₄H₅N = (Ni⁺ • 2C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	47.0	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: V⁺ + C₄H₅N = (V⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	>41.	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

+ Pyrrole = ( • Pyrrole )

By formula: W⁺ + C₄H₅N = (W⁺ • C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	>50.	kcal/mol	RAK	Gapeev and Yang, 2000	RCD

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Mass spectrum (electron ionization)

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

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Owner	NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved.
Origin	U.S. BUREAU OF MINES, LARAMIE, WYO, USA
NIST MS number	34529

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.

UV/Visible spectrum

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Data compiled by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

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Source	missing citation
Owner	INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved.
Origin	INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference	RAS UV No. 17
Instrument	Beckman DU
Melting point	-23.4
Boiling point	129.7

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, NIST Free Links, References, Notes

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

View large format table.

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	OV-101	110.	747.	Zhuravleva, 2000	50. m/0.3 mm/0.4 μm, He
Capillary	OV-101	110.	747.	Golovnya, Kuz'menko, et al., 1999	50. m/0.3 mm/0.4 μm, He
Packed	PMS-100	130.	706.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m
Packed	SE-30	110.	740.	Tibor and Anna, 1971	N2, Chromosorb W-AW; Column length: 2. m
Packed	SE-30	90.	733.	Tibor and Anna, 1971	N2, Chromosorb W-AW; Column length: 2. m

Kovats' RI, polar column, isothermal

View large format table.

Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	Carbowax 20M	160.	1516.	Kurbatova, Finkelstein, et al., 2004	Chromaton N-AW; Column length: 1. m
Packed	PEG-2000	150.	1492.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m
Packed	PEG-2000	152.	1520.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m
Packed	PEG-2000	179.	1530.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m
Packed	PEG-2000	180.	1514.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m
Packed	PEG-2000	200.	1520.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m
Packed	PEG-2000	200.	1545.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m
Packed	PEG-20M	110.	1502.	Tibor and Anna, 1971	N2, Chromosorb W-AW; Column length: 2. m
Packed	PEG-20M	90.	1498.	Tibor and Anna, 1971	N2, Chromosorb W-AW; Column length: 2. m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5	751.	Methven L., Tsoukka M., et al., 2007	60. m/0.32 mm/1. μm, 40. C @ 2. min, 4. K/min, 260. C @ 10. min
Capillary	HP-5	771.	Solina, Baumgartner, et al., 2005	25. m/0.2 mm/1. μm, He, 5. K/min, 280. C @ 5. min; T_start: 40. C
Capillary	HP-5	771.	Solina, Baumgartner, et al., 2005	25. m/0.2 mm/1. μm, He, 5. K/min, 280. C @ 5. min; T_start: 40. C
Capillary	SPB-5	757.	Pino, Marbot, et al., 2004	30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
Capillary	SPB-5	751.	Pino, Marbot, et al., 2004, 2	30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
Capillary	BPX-5	774.	Bredie, Mottram, et al., 2002	50. m/0.32 mm/0.5 μm, 60. C @ 5. min, 4. K/min, 250. C @ 20. min
Capillary	BPX-5	744.	Ames, Guy, et al., 2001	50. m/0.32 mm/0.5 μm, He, 60. C @ 5. min, 4. K/min, 250. C @ 10. min
Capillary	BPX-5	760.	Ames, Guy, et al., 2001, 2	50. m/0.32 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min, 250. C @ 10. min
Capillary	DB-1	731.	Kim, 2001	60. m/0.32 mm/1. μm, He, 40. C @ 5. min, 2. K/min; T_end: 220. C
Capillary	DB-1	733.	Izzo and Ho, 1991	50. m/0.32 mm/1.05 μm, He, 2. K/min, 260. C @ 40. min; T_start: 40. C
Packed	SE-30	739.	Peng, Ding, et al., 1988	He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m
Capillary	DB-1	727.	Zhang, Chien, et al., 1988	60. m/0.25 mm/0.25 μm, He, 2. K/min, 220. C @ 10. min; T_start: 40. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	CP-Sil 8CB-MS	759.	Elmore, Mottram, et al., 2000	60. m/0.25 mm/0.25 μm, He; Program: 0C(5min) => 40C/min => 40C (2min) => 4C/min => 280C
Capillary	DB-5	765.	Parker, Hassell, et al., 2000	50. m/0.32 mm/0.5 μm, He; Program: oC(5min) => 60C/min => 60C (5min) => 4C/min => 250C

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1521.	Lopez-Galilea I., Fournier N., et al., 2006	30. m/0.32 mm/0.5 μm, He, 5. K/min, 240. C @ 10. min; T_start: 40. C
Capillary	CP-Wax 52CB	1507.	Mahadevan and Farmer, 2006	60. C @ 5. min, 4. K/min, 220. C @ 30. min; Column length: 50. m; Column diameter: 0.32 mm
Capillary	Supelcowax-10	1523.	Chung, Yung, et al., 2002	60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min
Capillary	Supelcowax-10	1523.	Chung, Yung, et al., 2001	60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min
Capillary	DB-Wax	1513.	Kim, 2001	60. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 200. C @ 30. min
Capillary	Supelcowax-10	1524.	Chung, 2000	60. m/0.25 mm/0.25 μm, He, 2. K/min, 195. C @ 90. min; T_start: 35. C
Capillary	Supelcowax-10	1525.	Chung, 1999	60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min
Capillary	FFAP	1547.	Ott, Fay, et al., 1997	30. m/0.25 mm/0.25 μm, He, 20. C @ 1. min, 4. K/min, 200. C @ 1. min
Capillary	PEG-20M	1505.	Shimoda, Nakada, et al., 1997	60. m/0.25 mm/0.25 μm, He, 2. K/min, 230. C @ 60. min; T_start: 50. C
Capillary	DB-Wax	1505.	Shimoda, Shiratsuchi, et al., 1996	60. m/0.25 mm/0.25 μm, He, 2. K/min, 230. C @ 60. min; T_start: 50. C
Capillary	DB-Wax	1490.	Shimoda, Shigematsu, et al., 1995	60. m/0.25 mm/0.25 μm, 2. K/min; T_start: 50. C; T_end: 230. C
Capillary	DB-Wax	1538.	Chung, Eiserich, et al., 1994	He, 60. C @ 4. min, 3. K/min, 220. C @ 30. min; Column length: 60. m; Column diameter: 0.25 mm
Capillary	DB-Wax	1512.	Shiratsuchi, Shimoda, et al., 1994	60. m/0.25 mm/0.25 μm, 2. K/min, 230. C @ 60. min; T_start: 50. C
Capillary	DB-Wax	1512.	Shiratsuchi, Shimoda, et al., 1994, 2	60. m/0.25 mm/0.25 μm, He, 2. K/min, 230. C @ 60. min; T_start: 50. C
Capillary	Supelcowax-10	1514.	Chung and Cadwallader, 1993	60. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 195. C @ 40. min
Capillary	Supelcowax-10	1530.	Matiella and Hsieh, 1990	60. m/0.25 mm/0.25 μm, 40. C @ 5. min, 2. K/min, 175. C @ 20. min
Capillary	Supelcowax-10	1521.	Tanchotikul and Hsieh, 1989	60. m/0.25 mm/0.25 μm, 40. C @ 5. min, 2. K/min, 175. C @ 20. min
Capillary	Supelcowax-10	1523.	Tanchotikul and Hsieh, 1989	60. m/0.25 mm/0.25 μm, 40. C @ 5. min, 2. K/min, 175. C @ 20. min
Capillary	Supelcowax-10	1524.	Vejaphan, Hsieh, et al., 1988	60. m/0.25 mm/0.25 μm, 40. C @ 5. min, 2. K/min, 175. C @ 20. min
Capillary	Supelcowax-10	1526.	Vejaphan, Hsieh, et al., 1988	60. m/0.25 mm/0.25 μm, 40. C @ 5. min, 2. K/min, 175. C @ 20. min

Van Den Dool and Kratz RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Supelcowax-10	1525.	Bianchi, Careri, et al., 2007	30. m/0.25 mm/0.25 μm, He; Program: 35C(8min) => 4C/min => 60C => 6C/min => 160C => 20C/min => 200C(1min)
Capillary	CP-Wax 52CB	1513.	Alasalvar, Shahidi, et al., 2003	60. m/0.25 mm/0.25 μm, He; Program: 40C => 5C/min => 60C => 2.5C/min => 155C
Capillary	Supelcowax-10	1514.	Baek and Cadwallader, 1996	60. m/0.25 mm/0.25 μm; Program: 40C => (6C/min) => 80C(6min) => (15C/min) => 200C(10min)

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	VF-5 MS	750.	Leffingwell and Alford, 2011	60. m/0.32 mm/0.25 μm, Helium, 2. K/min, 260. C @ 28. min; T_start: 30. C
Capillary	VF-5 MS	757.	Leffingwell and Alford, 2011	60. m/0.32 mm/0.25 μm, Helium, 2. K/min, 260. C @ 28. min; T_start: 30. C
Capillary	HP-5	755.	Piyachaiseth, Jirapakkul, et al., 2011	60. m/0.25 mm/0.25 μm, Helium, 35. C @ 1. min, 10. K/min, 220. C @ 15. min
Capillary	ZB-5	751.	Harrison and Priest, 2009	30. m/0.25 mm/0.25 μm, Helium, 40. C @ 1. min, 6. K/min, 280. C @ 9. min
Capillary	SLB-5MS	768.	Risticevic, Carasek, et al., 2008	10. m/0.18 mm/0.18 μm, Helium, 40. C @ 1.5 min, 10. K/min; T_end: 295. C
Capillary	MDN-5	748.	van Loon, Linssen, et al., 2005	60. m/0.25 mm/0.25 μm, He, 40. C @ 4. min, 4. K/min, 270. C @ 5. min
Capillary	MDN-5	755.	van Loon, Linssen, et al., 2005	60. m/0.25 mm/0.25 μm, He, 40. C @ 4. min, 4. K/min, 270. C @ 5. min
Capillary	RTX-5	750.	Sies A., Hirsch R., et al., 2002	20. m/0.18 mm/0.4 μm, He, 20. C @ 3.5 min, 40. K/min, 290. C @ 0.5 min
Capillary	SPB-5	755.	Poligné, Collignan, et al., 2001	60. m/0.32 mm/1. μm, He, 3. K/min; T_start: 40. C; T_end: 200. C
Capillary	DB-1	725.	Buttery, Ling, et al., 1997	30. C @ 25. min, 4. K/min, 200. C @ 20. min; Column length: 60. m; Column diameter: 0.25 mm
Capillary	SE-54	765.	Bellesia, Pinetti, et al., 1996	25. m/0.2 mm/0.5 μm, He, 35. C @ 2. min, 5. K/min; T_end: 250. C
Capillary	DB-1	730.	Buttery and Ling, 1995	He, 30. C @ 25. min, 4. K/min, 200. C @ 20. min; Column length: 60. m; Column diameter: 0.25 mm
Capillary	DB-5	762.	Macku and Shibamoto, 1991	He, 40. C @ 5. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_end: 160. C
Capillary	DB-5	762.	Macku and Shibamoto, 1991, 2	He, 40. C @ 5. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_end: 160. C
Capillary	OV-101	768.	del Rosario, de Lumen, et al., 1984	He, 0. C @ 1. min, 3. K/min; Column length: 50. m; Column diameter: 0.31 mm; T_end: 225. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	SLB-5MS	739.	Risticevic, Carasek, et al., 2008	10. m/0.18 mm/0.18 μm, Helium; Program: not specified
Capillary	DB-5 MS	758.	Liu, Xu, et al., 2007	60. m/0.32 mm/1.0 μm, Helium; Program: 40 0C (2 min) 6 0C/min -> 100 0C 4 0C/min -> 180 0C 8 0C/min -> 250 0C (12 min)
Capillary	Polydimethyl siloxane with 5 % Ph groups	751.	Pino, Marbot, et al., 2005	Program: not specified
Capillary	SPB-5	749.	Begnaud, Pérès, et al., 2003	60. m/0.32 mm/1. μm; Program: not specified
Capillary	RTX-5 MS	758.	Machiels and Istasse, 2003	60. m/0.25 mm/0.5 μm, He; Program: 35C (3min) => 10C/min => 50C => 4C/min => 200C => 50C/min => 250C (10min)
Capillary	BPX-5	749.	Machiels, van Ruth, et al., 2003	60. m/0.32 mm/1. μm, He; Program: 40C (4min) => 2C/min => 90C => 4C/min => 130C => 8C/min => 250 C (10min)
Capillary	Methyl phenyl siloxane (not specified)	752.	Poligne, Collignan, et al., 2002	Program: not specified
Capillary	DB-5 MS	769.	Luo and Agnew, 2001	30. m/0.25 mm/1.0 μm, Helium; Program: not specified
Capillary	Methyl Silicone	723.	Zenkevich, 1999	Program: not specified
Capillary	SPB-1	733.	Flanagan, Streete, et al., 1997	60. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C
Capillary	SPB-1	733.	Strete, Ruprah, et al., 1992	60. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C
Capillary	SPB-1	755.	Strete, Ruprah, et al., 1992	60. m/0.53 mm/5.0 μm, Helium; Program: not specified
Capillary	DB-1	727.	Kawai, Ishida, et al., 1991	60. m/0.25 mm/0.25 μm; Program: not specified
Capillary	DB-1	728.	Kawai, Ishida, et al., 1991	60. m/0.25 mm/0.25 μm; Program: not specified
Capillary	OV-1	755.	Ramsey and Flanagan, 1982	Program: not specified

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax	1488.	Puvipirom and Chaisei, 2012	15. m/0.32 mm/0.50 μm, Helium, 3. K/min; T_start: 40. C; T_end: 250. C
Capillary	FFAP	1534.	Budryn, Nebesny, et al., 2011	30. m/0.32 mm/0.50 μm, Nitrogen, 35. C @ 5. min, 4. K/min, 250. C @ 45. min
Capillary	FFAP	1534.	Nebesny, Budryn, et al., 2007	30. m/0.32 mm/0.5 μm, N2, 35. C @ 5. min, 4. K/min, 320. C @ 45. min
Capillary	HP-Wax	1542.	Sanz, Maeztu, et al., 2002	60. m/0.25 mm/0.5 μm, He, 40. C @ 6. min, 3. K/min; T_end: 190. C
Capillary	HP-Wax	1542.	Maeztu, Sanz, et al., 2001	60. m/0.25 mm/0.5 μm, He, 40. C @ 6. min, 3. K/min; T_end: 190. C
Capillary	HP-Wax	1542.	Sanz, Ansorena, et al., 2001	60. m/0.25 mm/0.5 μm, He, 40. C @ 6. min, 3. K/min; T_end: 190. C
Capillary	Supelcowax-10	1526.	Girard and Durance, 2000	60. m/0.25 mm/0.25 μm, He, 35. C @ 10. min, 4. K/min; T_end: 200. C
Capillary	DB-Wax	1507.	Buttery, Orts, et al., 1999	30. C @ 4. min, 2. K/min, 170. C @ 60. min; Column length: 60. m; Column diameter: 0.32 mm
Capillary	DB-Wax	1507.	Buttery and Ling, 1998	30. C @ 4. min, 2. K/min, 170. C @ 30. min; Column length: 60. m; Column diameter: 0.25 mm
Capillary	PEG-20M	1477.	Kubota, Matsujage, et al., 1996	50. m/0.25 mm/0.25 μm, Nitrogen, 2. K/min; T_start: 60. C; T_end: 180. C
Capillary	DB-Wax	1513.	Umano, Hagi, et al., 1995	He, 40. C @ 2. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_end: 200. C
Capillary	DB-Wax	1470.	Hatsuko, Kazuko, et al., 1992	He, 60. C @ 10. min, 3. K/min; Column length: 30. m; Column diameter: 0.25 mm; T_end: 240. C
Capillary	DB-Wax	1509.	Wong and Bernhard, 1988	He, 70. C @ 8. min, 2. K/min; Column length: 30. m; Column diameter: 0.25 mm; T_end: 160. C
Capillary	Carbowax 20M	1504.	Shibamoto and Russell, 1977	1. K/min; Column length: 100. m; Column diameter: 0.25 mm; T_start: 70. C; T_end: 170. C
Capillary	Carbowax 20M	1505.	Shibamoto and Russell, 1977	1. K/min; Column length: 100. m; Column diameter: 0.25 mm; T_start: 70. C; T_end: 170. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1498.	Welke, Manfroi, et al., 2012	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	DB-Wax	1507.	Welke, Manfroi, et al., 2012	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	DB-Wax	1518.	Gonzalez-Rios, Suarez-Quiroz, et al., 2007	30. m/0.25 mm/0.25 μm, Hydrogen; Program: 44 0C 3 0C/min -> 170 0C 8 0C/min -> 250 0C
Capillary	DB-Wax	1514.	Kim. J.H., Ahn, et al., 2004	60. m/0.25 mm/0.25 μm, Helium; Program: 60 0C (3 min) 2 0C/min -> 150 0C 4 0C/min -> 200 0C
Capillary	Carbowax 20M	1516.	Finkelstein, Kurbatova, et al., 2002	Program: not specified
Capillary	CP-Wax 52CB	1532.	Muresan, Eillebrecht, et al., 2000	50. m/0.32 mm/1.2 μm; Program: 40C(10min) => 3C/min => 190C => 10C/min => 250C(5min)
Capillary	Supelcowax-10	1524.	Chang, Seitz, et al., 1995	30. m/0.32 mm/0.25 μm, He; Program: 50C(2min) => 7C/min => 140C => 17.5C/min => 230C
Capillary	DB-Wax	1508.	Peng, Yang, et al., 1991	Program: not specified
Capillary	DB-Wax	1511.	Peng, Yang, et al., 1991	Program: not specified
Capillary	Carbowax 20M	1472.	Ramsey and Flanagan, 1982	Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, Notes

Zaheeruddin and Lodhi, 1991
Zaheeruddin, M.; Lodhi, Z.H., Enthalpies of formation of some cyclic compounds, Phys. Chem. (Peshawar Pak.), 1991, 10, 111-118. [all data]

Scott, Berg, et al., 1967
Scott, D.W.; Berg, W.T.; Hossenlopp, I.A.; Hubbard, W.N.; Messerly, J.F.; Todd, S.S.; Douslin, D.R.; McCullough, J.P.; Waddington, G., Pyrrole: Chemical thermodynamic properties, J. Phys. Chem., 1967, 71, 2263-2270. [all data]

Zimmerman and Geisenfelder, 1961
Zimmerman, H.; Geisenfelder, H., Uber die Mesomerieenergie von Azolen, Z. Electrochem., 1961, 65, 368-371. [all data]

Rosso and Carbonnel, 1973
Rosso, M.J.-C.; Carbonnel, L., Hydrates + cubic clathrates generated by the nitrogenous meterocycles: the binary systems water + propylene imine and water + pyrrole, C. R. Seances Acad. Sci., Ser. C, 1973, 277, 259. [all data]

Timmermans and Hennaut-Roland, 1955
Timmermans, J.; Hennaut-Roland, M., Work of the International Bureau of Physical-Chemical Standards. IX. The Physical Constants of Twenty Organic Compounds, J. Chim. Phys. Phys.-Chim. Biol., 1955, 52, 223. [all data]

Anonymous, 1942
Anonymous, R., , Am. Pet. Inst. Res. Proj. 6, Natl. Bur. Stand., 1942. [all data]

Milazzo, 1941
Milazzo, G., Boll. Sci. Facolta Chim. Ind. Bologna, 1941, 94. [all data]

Scott, Berg, et al., 1967, 2
Scott, D.W.; Berg, W.T.; Hossenlopp, I.A.; Hubbard, W.N.; Messerly, J.F.; Todd, S.S.; Douslin, D.R.; McCullough, J.P.; Waddington, G., Pyrrole: Chemical Thermodynamic Properties, J. Phys. Chem., 1967, 71, 2263. [all data]

Helm, Lanum, et al., 1958
Helm, R.V.; Lanum, W.J.; Cook, G.L.; Ball, J.S., Purification and Properties of Pyrrole, Pyrrolidine, Pyridine and 2-Methylpyridine, J. Phys. Chem., 1958, 62, 858. [all data]

McCullough and Waddington, 1957
McCullough, J.P.; Waddington, G., Melting-point purity determinations: limitations as evidenced by calorimetric studies in the melting region, Anal. Chim. Acta, 1957, 17, 80. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Cheng, McCoubrey, et al., 1962
Cheng, D.C.H.; McCoubrey, J.C.; Phillips, D.G., Critical Temperatures of Some Organic Cyclic Compounds, Trans. Faraday Soc., 1962, 58, 224. [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [all data]

Kimizuka and Szydlowski, 1992
Kimizuka, Wieslawa; Szydlowski, Jerzy, Vapor pressure isotope effect of n-deuterated pyrrole, Fluid Phase Equilibria, 1992, 77, 261-267, https://doi.org/10.1016/0378-3812(92)85107-J . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Osborn and Douslin, 1968
Osborn, Ann G.; Douslin, Donald R., Vapor pressure relations of 13 nitrogen compounds related to petroleum, J. Chem. Eng. Data, 1968, 13, 4, 534-537, https://doi.org/10.1021/je60039a024 . [all data]

Eon, Pommier, et al., 1971
Eon, C.; Pommier, C.; Guiochon, G., Vapor pressures and second virial coefficients of some five-membered heterocyclic derivatives, J. Chem. Eng. Data, 1971, 16, 4, 408-410, https://doi.org/10.1021/je60051a008 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Gianola, Ichino, et al., 2004
Gianola, A.J.; Ichino, T.; Hoenigman, R.L.; Kato, S.; Bierbaum, V.M.; Lineberger, W.C., Thermochemistry and electronic structure of the pyrrolyl radical, J. Phys. Chem. A, 2004, 108, 46, 10326-10335, https://doi.org/10.1021/jp047790+ . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Khatymov, R.V.; Mazunov, V.A.; Takhistov, V.V.; Travkin, O.V.; Yakovleva, E.V., Thermochemistry of negatively charged ions. II. Energetics of formation of negative ions from acridanone and some of its derivatives, Rapid Commun. Mass Spectrom., 1999, 13, 10, 912-923, https://doi.org/10.1002/(SICI)1097-0231(19990530)13:10<912::AID-RCM585>3.0.CO;2-W . [all data]

Meot-ner, 1988
Meot-ner, M., Ionic Hydrogen Bond and Ion Solvation. ₆. Interaction Energies of the Acetate Ion with Organic Molecules. Comparison of CH₃COO^- with Cl^-, CN^-, and SH^-, J. Am. Chem. Soc., 1988, 110, 12, 3854, https://doi.org/10.1021/ja00220a022 . [all data]

Larson and McMahon, 1987
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. The energetics of interaction between cyanide ion and bronsted acids, J. Am. Chem. Soc., 1987, 109, 6230. [all data]

Payzant, Yamdagni, et al., 1971
Payzant, J.D.; Yamdagni, R.; Kebarle, P., Hydration of CN-, NO₂-, NO₃-, and HO- in the gas phase, Can. J. Chem., 1971, 49, 3308. [all data]

Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P., Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions, J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014 . [all data]

Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria, J. Am. Chem. Soc., 1984, 106, 517. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Meot-ner, 1988, 2
Meot-ner, M., The Ionic Hydrogen Bond and Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules, J. Am. Chem. Soc., 1988, 110, 12, 3858, https://doi.org/10.1021/ja00220a022 . [all data]

Hiraoka, Takimoto, et al., 1987
Hiraoka, K.; Takimoto, H.; Yamabe, S., Stabilities and Structures in Cluster Ions of Five-Membered Heterocyclic Compounds Containing O, N and S Atoms, J. Am. Chem. Soc., 1987, 109, 24, 7346, https://doi.org/10.1021/ja00258a018 . [all data]

Deakyne and Meot-Ner (Mautner), 1985
Deakyne, C.A.; Meot-Ner (Mautner), M., Unconventional Ionic Hydrogen Bonds. 2. NH+ pi. Complexes of Onium Ions with Olefins and Benzene Derivatives, J. Am. Chem. Soc., 1985, 107, 2, 474, https://doi.org/10.1021/ja00288a034 . [all data]

Meot-Ner (Mautner), 1988
Meot-Ner (Mautner), M., Models for Strong Interactions in Proteins and Enzymes. 2. Interactions of Ions with the Peptide Link and Imidazole, J. Am. Chem. Soc., 1988, 110, 10, 3075, https://doi.org/10.1021/ja00218a014 . [all data]

Gapeev and Yang, 2000
Gapeev, A.; Yang, C.-N., Binding Energies of Gas-Phase Ions with Pyrrole. Experimental and Quantum Chemical Results, J. Phys. Chem. A, 2000, 104, 14, 3246, https://doi.org/10.1021/jp992627d . [all data]

Huang and Rodgers, 2002
Huang, H.; Rodgers, M.T., Sigma versus Pi interactions in alkali metal ion binding to azoles: Threshold collision-induced dissociation and ab initio theory studies, J. Phys. Chem. A, 2002, 106, 16, 4277, https://doi.org/10.1021/jp013630b . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Klasinc, Sabljic, et al., 1982
Klasinc, L.; Sabljic, A.; Kluge, G.; Rieger, J.; Scholz, M., Chemistry of excited states. Part 13. Assignment of lowest .PI.-ionizations in photoelectron spectra of thiophen, furan, and pyrrole, J. Chem. Soc. Perkin Trans. 2, 1982, 539. [all data]

Galasso, Klasinc, et al., 1981
Galasso, V.; Klasinc, L.; Sabluic, A.; Trinajstic, N.; Pappalardo, G.C.; Steglich, W., Conformation and photoelectron spectra of 2-(2-Furyl)pyrrole and 2-(2-tThienyl)pyrrole, J. Chem. Soc. Perkin Trans. 2, 1981, 127. [all data]

Willett and Baer, 1980
Willett, G.D.; Baer, T., Thermochemistry and dissociation dynamics of state-selected C₄H₄X ions. 3. C₄H₅N⁺, J. Am. Chem. Soc., 1980, 102, 6774. [all data]

Tedder and Vidaud, 1980
Tedder, J.M.; Vidaud, P.H., Charge exchange mass spectra of thiophene, pyrrole and furan, J. Chem. Soc. Faraday Trans. 2, 1980, 76, 1516. [all data]

Cooper, Williamson, et al., 1980
Cooper, C.D.; Williamson, A.D.; Miller, J.C.; Compton, R.N., Resonantly enhanced multiphoton ionization of pyrrole, N-methyl pyrrole, and furan, J. Chem. Phys., 1980, 73, 1527. [all data]

Williamson, Compton, et al., 1979
Williamson, A.D.; Compton, R.N.; Eland, J.H.D., Accurate photoionization thresholds by multiphoton ionization: Pyrrole, J. Chem. Phys., 1979, 70, 590. [all data]

Van Veen, 1976
Van Veen, E.H., Triplet π-π^* transitions in thiophene, furan and pyrrole by low-energy electron-impact spectroscopy, Chem. Phys. Lett., 1976, 41, 535. [all data]

Thorstad and Undheim, 1974
Thorstad, O.; Undheim, K., Mass spectrometry of onium compounds. XXIV. Ionisation potential in structure analysis of pyridodiazo-oxides, Chem. Scr., 1974, 6, 222. [all data]

Linda, Marino, et al., 1971
Linda, P.; Marino, G.; Pignataro, S., A comparison of sensitivities to substituent effects of five- membered heteroaromatic rings in gas phase ionization, J. Chem. Soc. B, 1971, 1585. [all data]

Derrick, Asbrink, et al., 1971
Derrick, P.J.; Asbrink, L.; Edqvist, O.; Jonsson, B.-O.; Lindholm, E., Rydberg series in small molecules. XII. Photoelectron spectroscopy and electronic structure of pyrrole, Intern. J. Mass Spectrom. Ion Phys., 1971, 6, 191. [all data]

Potapov and Yuzhakova, 1970
Potapov, V.K.; Yuzhakova, O.A., Photoionization and electronic structure of pyrrole and its methyl derivatives, Dokl. Akad. Nauk SSSR, 1970, 192, 131, In original 365. [all data]

Potapov and Bazhenov, 1970
Potapov, V.K.; Bazhenov, B.A., The photionization of pyrrole, furan, and thiophene, High Energy Chem., 1970, 505, In original 553. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Cradock, Findlay, et al., 1973
Cradock, S.; Findlay, R.H.; Palmer, M.H., The molecular energy levels of the azoles: A study by photoelectron spectroscopy and ab initio molecular orbital calculations, Tetrahedron, 1973, 29, 2173. [all data]

Sakurai and Jennings, 1981
Sakurai, H.; Jennings, K.R., A study of the structures of decomposing and non-decomposing [C₄H₅N]⁺ ions formed from different neutral species, Org. Mass Spectrom., 1981, 16, 393. [all data]

Zhuravleva, 2000
Zhuravleva, I.L., Evaluation of the polarity and boiling points of nitrogen-containing heterocyclic compounds by gas chromatography, Russ. Chem. Bull. (Engl. Transl.), 2000, 49, 2, 325-328, https://doi.org/10.1007/BF02494682 . [all data]

Golovnya, Kuz'menko, et al., 1999
Golovnya, R.V.; Kuz'menko, T.E.; Zhuravleva, I.L., Gas chromatographic indicator of the ability of five- and six-membered heterocyclic nitrogen-containing compounds for self-association in pure liquids, Russ. Chem. Bull. (Engl. Transl.), 1999, 48, 4, 726-729, https://doi.org/10.1007/BF02496256 . [all data]

Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases, Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]

Tibor and Anna, 1971
Tibor, T.; Anna, B., Gázkromatográfiás retenció és a kémiai szerkezet, I., Magy. Kem. Foly., 1971, 77, 576-587. [all data]

Kurbatova, Finkelstein, et al., 2004
Kurbatova, S.V.; Finkelstein, E.E.; Kolosova, E.A.; Kartashev, A.V.; Rashkin, S.V., Structural analogy method in studies of adamantanes, J. Struct. Chem., 2004, 45, 1, 144-150, https://doi.org/10.1023/B:JORY.0000041513.82837.4e . [all data]

Methven L., Tsoukka M., et al., 2007
Methven L.; Tsoukka M.; Oruna-Concha M.J.; Parker J.K.; Mottram D.S., Influence of sulfur amino acids on the volatile and nonvolatile components of cooked salmon (Salmo salar), J. Agric. Food Chem., 2007, 55, 4, 1427-1436, https://doi.org/10.1021/jf0625611 . [all data]

Solina, Baumgartner, et al., 2005
Solina, M.; Baumgartner, P.; Johnson, R.L.; Whitfield, F.B., Volatile aroma components of soy protein isolate and acid-hydrolysed vegetable protein, Food Chem., 2005, 90, 4, 861-873, https://doi.org/10.1016/j.foodchem.2004.06.005 . [all data]

Pino, Marbot, et al., 2004
Pino, J.A.; Marbot, R.; Vazquez, C., Volatile components of tamarind (Tamarindus indica L.) grown in Cuba, J. Essent. Oil Res., 2004, 16, 4, 318-320, https://doi.org/10.1080/10412905.2004.9698731 . [all data]

Pino, Marbot, et al., 2004, 2
Pino, J.A.; Marbot, R.; Rosado, A.; Vázquez, C., Volatile constituents of Malay rose apple [Syzygium malaccense (L.) Merr. Perry], Flavour Fragr. J., 2004, 19, 1, 32-35, https://doi.org/10.1002/ffj.1269 . [all data]

Bredie, Mottram, et al., 2002
Bredie, W.L.P.; Mottram, D.S.; Guy, R.C.E., Effect of temperature and pH on the generation of flavor volatiles in extrusion cooking of wheat flour, J. Agric. Food Chem., 2002, 50, 5, 1118-1125, https://doi.org/10.1021/jf0111662 . [all data]

Ames, Guy, et al., 2001
Ames, J.M.; Guy, R.C.E.; Kipping, G.J., Effect of pH and temperature on the formation of volatile compounds in cysteine/reducing sugar/starch mixtures during extrusion cooking, J. Agric. Food Chem., 2001, 49, 4, 1885-1894, https://doi.org/10.1021/jf0012547 . [all data]

Ames, Guy, et al., 2001, 2
Ames, J.M.; Guy, R.C.E.; Kipping, G.J., Effect of pH, temperature, and moisture on the formation of volatile compounds in glycine/glucose model systems, J. Agric. Food Chem., 2001, 49, 9, 4315-4323, https://doi.org/10.1021/jf010198m . [all data]

Kim, 2001
Kim, J.S., Einfluss der Temperatur beim Rösten von Sesam auf Aroma und antioxidative Eigenschaften des Öls, PhD Thesis, Technischen Universität Berlin zur Erlangung des akademischen Grades, Berlin, 2001, 151. [all data]

Izzo and Ho, 1991
Izzo, H.V.; Ho, C.-T., Isolation and identification of the volatile components of an extruded autolyzed yeast extract, J. Agric. Food Chem., 1991, 39, 12, 2245-2248, https://doi.org/10.1021/jf00012a029 . [all data]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [all data]

Zhang, Chien, et al., 1988
Zhang, Y.; Chien, M.; Ho.C.-T., Comparison of the volatile compounds obtained from thermal degradation of cysteine and glutathione in water, J. Agric. Food Chem., 1988, 36, 5, 992-996, https://doi.org/10.1021/jf00083a022 . [all data]

Elmore, Mottram, et al., 2000
Elmore, J.S.; Mottram, D.S.; Enser, M.; Wood, J.D., The effects of diet and breed on the volatile compounds of cooked lamb, Meat Sci., 2000, 55, 2, 149-159, https://doi.org/10.1016/S0309-1740(99)00137-0 . [all data]

Parker, Hassell, et al., 2000
Parker, J.K.; Hassell, G.M.E.; Mottram, D.S.; Guy, R.C.E., Sensory and instrumental analyses of volatiles generated during the extrusion cooking of oat flours, J. Agric. Food Chem., 2000, 48, 8, 3497-3506, https://doi.org/10.1021/jf991302r . [all data]

Lopez-Galilea I., Fournier N., et al., 2006
Lopez-Galilea I.; Fournier N.; Cid C.; Guichard E., Changes in headspace volatile concentrations of coffee brews caused by the roasting process and the brewing procedure, J. Agric. Food Chem., 2006, 54, 22, 8560-8566, https://doi.org/10.1021/jf061178t . [all data]

Mahadevan and Farmer, 2006
Mahadevan, K.; Farmer, L., Key Odor Impact Compounds in Three Yeast Extract Pastes, J. Agric. Food Chem., 2006, 54, 19, 7242-7250, https://doi.org/10.1021/jf061102x . [all data]

Chung, Yung, et al., 2002
Chung, H.-Y.; Yung, I.K.S.; Ma, W.C.J.; Kim, J.-S., Analysis of volatile components in frozen and dried scallops (Patinopecten yessoensis) by gas chromatography/mass spectrometry, Food Res. Int., 2002, 35, 1, 43-53, https://doi.org/10.1016/S0963-9969(01)00107-7 . [all data]

Chung, Yung, et al., 2001
Chung, H.Y.; Yung, I.K.S.; Kim, J.-S., Comparison of volatile components in dried scallops (Chlamys farreri and Patinopecten yessoensis) prepared by boiling and steaming methods, J. Agric. Food Chem., 2001, 49, 1, 192-202, https://doi.org/10.1021/jf000692a . [all data]

Chung, 2000
Chung, H.Y., Volatile flavor components in red fermented soybean (Glycine max) curds, J. Agric. Food Chem., 2000, 48, 5, 1803-1809, https://doi.org/10.1021/jf991272s . [all data]

Chung, 1999
Chung, H.Y., Volatile components in crabmeats of Charybdis feriatus, J. Agric. Food Chem., 1999, 47, 6, 2280-2287, https://doi.org/10.1021/jf981027t . [all data]

Ott, Fay, et al., 1997
Ott, A.; Fay, L.B.; Chaintreau, A., Determination and origin of the aroma impact compounds of yogurt flavor, J. Agric. Food Chem., 1997, 45, 3, 850-858, https://doi.org/10.1021/jf960508e . [all data]

Shimoda, Nakada, et al., 1997
Shimoda, M.; Nakada, Y.; Nakashima, M.; Osajima, Y., Quantitative comparison of volatile flavor compounds in deep-roasted and light-roasted sesame seed oil, J. Agric. Food Chem., 1997, 45, 8, 3193-3196, https://doi.org/10.1021/jf970172o . [all data]

Shimoda, Shiratsuchi, et al., 1996
Shimoda, M.; Shiratsuchi, H.; Nakada, Y.; Wu, Y.; Osajima, Y., Identification and sensory characterization of volatile flavor compounds in sesame seed oil, J. Agric. Food Chem., 1996, 44, 12, 3909-3912, https://doi.org/10.1021/jf960115f . [all data]

Shimoda, Shigematsu, et al., 1995
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y., Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusion, J. Agric. Food Chem., 1995, 43, 6, 1616-1620, https://doi.org/10.1021/jf00054a037 . [all data]

Chung, Eiserich, et al., 1994
Chung, T.Y.; Eiserich, J.P.; Shibamoto, T., Volatile compounds produced from peanut oil heated with different amounts of cysteine, J. Agric. Food Chem., 1994, 42, 8, 1743-1746, https://doi.org/10.1021/jf00044a032 . [all data]

Shiratsuchi, Shimoda, et al., 1994
Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y., Off-flavor compounds in spray-dried skim milk powder, J. Agric. Food Chem., 1994, 42, 6, 1323-1327, https://doi.org/10.1021/jf00042a014 . [all data]

Shiratsuchi, Shimoda, et al., 1994, 2
Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y., Volatile flavor compounds in spray-dried skim milk powder, J. Agric. Food Chem., 1994, 42, 4, 984-988, https://doi.org/10.1021/jf00040a028 . [all data]

Chung and Cadwallader, 1993
Chung, H.Y.; Cadwallader, K.R., Volatile components in blue crab (Callinectes sapidus) meat and processing by-product, J. Food Sci., 1993, 58, 6, 1203-1207, https://doi.org/10.1111/j.1365-2621.1993.tb06148.x . [all data]

Matiella and Hsieh, 1990
Matiella, J.E.; Hsieh, T.C.-Y., Analysis of crabmeat volatile compounds, J. Food Sci., 1990, 55, 4, 962-966, https://doi.org/10.1111/j.1365-2621.1990.tb01575.x . [all data]

Tanchotikul and Hsieh, 1989
Tanchotikul, U.; Hsieh, T.C.-Y., Volatile Flavor Components in Crayfish Waste, J. Food Sci., 1989, 54, 6, 1515-1520, https://doi.org/10.1111/j.1365-2621.1989.tb05149.x . [all data]

Vejaphan, Hsieh, et al., 1988
Vejaphan, W.; Hsieh, T.C.Y.; Williams, S.S., Volatile flavor components from boiled crayfish (Procambarus clarkii) tail meat, J. Food Sci., 1988, 53, 6, 1666-1670, https://doi.org/10.1111/j.1365-2621.1988.tb07811.x . [all data]

Bianchi, Careri, et al., 2007
Bianchi, F.; Careri, M.; Mangia, A.; Musci, M., Retention indices in the analysis of food aroma volatile compounds in temperature-programmed gas chromatography: Database creation and evaluation of precision and robustness, J. Sep. Sci., 2007, 39, 4, 563-572, https://doi.org/10.1002/jssc.200600393 . [all data]

Alasalvar, Shahidi, et al., 2003
Alasalvar, C.; Shahidi, F.; Cadwallader, K.R., Comparison of natural and roasted Turkish Tombul hazelnut (Corylus avellana L.) volatiles and flavor by DHA/GC/MS and descriptive sensory analysis, J. Agric. Food Chem., 2003, 51, 17, 5067-5072, https://doi.org/10.1021/jf0300846 . [all data]

Baek and Cadwallader, 1996
Baek, H.H.; Cadwallader, K.R., Volatile compounds in flavor concentrates produced from crayfish-processing byproducts with and without protease treatment, J. Agric. Food Chem., 1996, 44, 10, 3262-3267, https://doi.org/10.1021/jf960023q . [all data]

Leffingwell and Alford, 2011
Leffingwell, J.; Alford, E.D., Volatile constituents of the giant pufball mushroom (Calvatia gigantea), Leffingwell Rep., 2011, 4, 1-17. [all data]

Piyachaiseth, Jirapakkul, et al., 2011
Piyachaiseth, T.; Jirapakkul, W.; Chaiseri, S., Aroma compounds of flash-fried rice, Kasetsart J. (Nat. Sci.), 2011, 45, 717-729. [all data]

Harrison and Priest, 2009
Harrison, B.M.; Priest, F.G., Composition of peaks used in the preparation of malt for Scotch Whisky production - influence of geographical source and extraction depth, J. Agric. Food Chem., 2009, 57, 6, 2385-2391, https://doi.org/10.1021/jf803556y . [all data]

Risticevic, Carasek, et al., 2008
Risticevic, S.; Carasek, E.; Pawliszyn, J., Headspace solid-phase microextraction-gas chromatographic-time-of-flight mass spectrometric methodology for geographical origin verification of coffee, Anal. Chim. Acta, 2008, 617, 1-2, 72-84, https://doi.org/10.1016/j.aca.2008.04.009 . [all data]

van Loon, Linssen, et al., 2005
van Loon, W.A.M.; Linssen, J.P.H.; Legger, A.; Posthumus, M.A.; Voragen, A.G.J., Identification and olfactometry of French fries flavour extracted at mouth conditions, Food Chem., 2005, 90, 3, 417-425, https://doi.org/10.1016/j.foodchem.2004.05.005 . [all data]

Sies A., Hirsch R., et al., 2002
Sies A.; Hirsch R.; Löscher R.; Tablack P.; Guth H., Direct thermal desorption and Fast-GC-TOF-MS for a rapid quality control of hazelnuts, 10th Weurman Flavour Research Symposium, 24 - 28 June 2002, Beaune, France, 2002. [all data]

Poligné, Collignan, et al., 2001
Poligné, I.; Collignan, A.; Trystram, G., Characterization of traditional processing of pork meat into boucané, Meat Sci., 2001, 59, 4, 377-389, https://doi.org/10.1016/S0309-1740(01)00090-0 . [all data]

Buttery, Ling, et al., 1997
Buttery, R.G.; Ling, L.C.; Stern, D.J., Studies on popcorn aroma and flavor volatiles, J. Agric. Food Chem., 1997, 45, 3, 837-843, https://doi.org/10.1021/jf9604807 . [all data]

Bellesia, Pinetti, et al., 1996
Bellesia, F.; Pinetti, A.; Bianchi, A.; Tirillini, B., Volatile compounds of the white truffle (Tuber magnaturn Pico) from middle Italy, Flavour Fragr. J., 1996, 11, 4, 239-243, https://doi.org/10.1002/(SICI)1099-1026(199607)11:4<239::AID-FFJ573>3.0.CO;2-A . [all data]

Buttery and Ling, 1995
Buttery, R.G.; Ling, L.C., Volatile flavor components of corn tortillas and related products, J. Agric. Food Chem., 1995, 43, 7, 1878-1882, https://doi.org/10.1021/jf00055a023 . [all data]

Macku and Shibamoto, 1991
Macku, C.; Shibamoto, T., Headspace volatile compounds formed from heated corn oil and corn oil with glycine, J. Agric. Food Chem., 1991, 39, 7, 1265-1269, https://doi.org/10.1021/jf00007a014 . [all data]

Macku and Shibamoto, 1991, 2
Macku, C.; Shibamoto, T., Volatile sulfur-containing compounds generated from the thermal interaction of corn oil and cysteine, J. Agric. Food Chem., 1991, 39, 11, 1987-1989, https://doi.org/10.1021/jf00011a021 . [all data]

del Rosario, de Lumen, et al., 1984
del Rosario, R.; de Lumen, B.O.; Habu, T.; Flath, R.A.; Mon, T.R.; Teranishi, R., Comparison of headspace volatiles from winged beans and soybeans, J. Agric. Food Chem., 1984, 32, 5, 1011-1015, https://doi.org/10.1021/jf00125a015 . [all data]

Liu, Xu, et al., 2007
Liu, Y.; Xu, X.-L.; Zhou, G.-H., Comparative study of volatile compounds in traditional Chinese Nanjing marinated duck by different extraction techniques, Int. J. Food Sci. Technol., 2007, 42, 5, 543-550, https://doi.org/10.1111/j.1365-2621.2006.01264.x . [all data]

Pino, Marbot, et al., 2005
Pino, J.A.; Marbot, R.; Rosado, A.; Vázquez, C., Volatile constituents of Malay rose apple [Syzygium malaccense (L.) Merr. Perry], Flavour Fragr. J., 2005, 20, 98-100. [all data]

Begnaud, Pérès, et al., 2003
Begnaud, F.; Pérès, C.; Berdagué, J.-L., Characterization of volatile effluents of livestock buildings by solid-phase microextraction, Int. J. Environ. Anal. Chem., 2003, 83, 10, 837-849, https://doi.org/10.1080/03067310310001603349 . [all data]

Machiels and Istasse, 2003
Machiels, D.; Istasse, L., Evaluation of two commercial solid-phase microextraction fibres for the analysis of target aroma compounds in cooked beef meat, Talanta, 2003, 61, 4, 529-537, https://doi.org/10.1016/S0039-9140(03)00319-9 . [all data]

Machiels, van Ruth, et al., 2003
Machiels, D.; van Ruth, S.M.; Posthumus, M.A.; Istasse, L., Gas chromatography-olfactometry analysis of the volatile compounds of two commercial Irish beef meats, Talanta, 2003, 60, 4, 755-764, https://doi.org/10.1016/S0039-9140(03)00133-4 . [all data]

Poligne, Collignan, et al., 2002
Poligne, I.; Collignan, A.; Trystram, G., Effects of salting, drying, cooking, and smoking operations on volatile compound formation and collor patterns in pork, Food Eng. Physical Properties, 2002, 67, 8, 2976-2986. [all data]

Luo and Agnew, 2001
Luo, J.; Agnew, M.P., Gas characteristics before and after biofiltration treating odorous emissions from animal rendering processes, Environ. Technol., 2001, 22, 9, 1091-1103, https://doi.org/10.1080/09593332208618220 . [all data]

Zenkevich, 1999
Zenkevich, I.G., Precalculation of Gas Chromatographic Retention Indices of Organic Compounds from Boiling Points of their Structural Analogues, Zh. Struct. Khim., 1999, 40, 1, 121-130. [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technical_series₁997-01-01₁.pdf. [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [all data]

Kawai, Ishida, et al., 1991
Kawai, T.; Ishida, Y.; Kakiuchi, H.; Ikeda, N.; Higashida, T.; Nakamura, S., Flavor components of dried squid, J. Agric. Food Chem., 1991, 39, 4, 770-777, https://doi.org/10.1021/jf00004a031 . [all data]

Ramsey and Flanagan, 1982
Ramsey, J.D.; Flanagan, R.J., Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse, J. Chromatogr., 1982, 240, 2, 423-444, https://doi.org/10.1016/S0021-9673(00)99622-5 . [all data]

Puvipirom and Chaisei, 2012
Puvipirom, J.; Chaisei, S., Contribution of roasted grains and seeds in aroma of oleang (Thai coffee drink), Int. Food Res. J., 2012, 19, 2, 583-588. [all data]

Budryn, Nebesny, et al., 2011
Budryn, G.; Nebesny, E.; Kula, J.; Majda, T.; Krysiak, W., HS-SPME/GC/MS Profiles of convectively and microwave roasted Ivory Coast Robusta coffee brews, Czech. J. Food Sci., 2011, 29, 2, 151-160. [all data]

Nebesny, Budryn, et al., 2007
Nebesny, E.; Budryn, G.; Kula, J.; Majda, T., The effect of roasting method on headspace composition of robusta coffee bean aroma, Eur. Food Res. Technol., 2007, 225, 1, 9-19, https://doi.org/10.1007/s00217-006-0375-0 . [all data]

Sanz, Maeztu, et al., 2002
Sanz, C.; Maeztu, L.; Zapelena, M.J.; Bello, J.; Cid, C., Profiles of volatile compounds and sensory analysis of three blends of coffee: influence of different proportions of Arabica and Robusta and influence of roasting coffee with sugar, J. Sci. Food Agric., 2002, 82, 8, 840-847, https://doi.org/10.1002/jsfa.1110 . [all data]

Maeztu, Sanz, et al., 2001
Maeztu, L.; Sanz, C.; Andueza, S.; de Peña, M.P.; Bello, J.; Cid, C., Characterization of espresso coffee aroma by static headspace GC-MS and sensory flavor profile, J. Agric. Food Chem., 2001, 49, 11, 5437-5444, https://doi.org/10.1021/jf0107959 . [all data]

Sanz, Ansorena, et al., 2001
Sanz, C.; Ansorena, D.; Bello, J.; Cid, C., Optimizing headspace temperature and time sampling for identification of volatile compounds in ground roasted Arabica coffee, J. Agric. Food Chem., 2001, 49, 3, 1364-1369, https://doi.org/10.1021/jf001100r . [all data]

Girard and Durance, 2000
Girard, B.; Durance, T., Headspace volatiles of sockeye and pink salmon as affected by retort process, Food Chem. Toxicol., 2000, 65, 1, 34-39. [all data]

Buttery, Orts, et al., 1999
Buttery, R.G.; Orts, W.J.; Takeoka, G.R.; Nam, Y., Volatile flavor components of rice cakes, J. Agric. Food Chem., 1999, 47, 10, 4353-4356, https://doi.org/10.1021/jf990140w . [all data]

Buttery and Ling, 1998
Buttery, R.G.; Ling, L.C., Additional studies on flavor components of corn tortilla chips, J. Agric. Food Chem., 1998, 46, 7, 2764-2769, https://doi.org/10.1021/jf980125b . [all data]

Kubota, Matsujage, et al., 1996
Kubota, K.; Matsujage, Y.; Sekiwa, Y.; Kobayashi, A., Identification of the characteristic volatile flavor compounds formed by cooking squid (Todarodes pacificus Steenstrup), Food Sci. Technol., 1996, 2, 3, 163-166. [all data]

Umano, Hagi, et al., 1995
Umano, K.; Hagi, Y.; Nakahara, K.; Shyoji, A.; Shibamoto, T., Volatile chemicals formed in the headspace of a heated D-glucose/L-cysteine Maillard model system, J. Agric. Food Chem., 1995, 43, 8, 2212-2218, https://doi.org/10.1021/jf00056a046 . [all data]

Hatsuko, Kazuko, et al., 1992
Hatsuko, S.; Kazuko, H.; Masayoshi, K.; Yoshiaki, I., Improvement of quality of likorine extract by heat treatment, J. Food Sci. Technol., 1992, 39, 11, 976-983, https://doi.org/10.3136/nskkk1962.39.976 . [all data]

Wong and Bernhard, 1988
Wong, J.M.; Bernhard, R.A., Effect of nitrogen source on pyrazine formation, J. Agric. Food Chem., 1988, 36, 1, 123-129, https://doi.org/10.1021/jf00079a032 . [all data]

Shibamoto and Russell, 1977
Shibamoto, T.; Russell, G.F., A study of the volatiles isolated from a D-glucose-hydrogen sulfide-ammonia model system, J. Agric. Food Chem., 1977, 25, 1, 109-112, https://doi.org/10.1021/jf60209a054 . [all data]

Welke, Manfroi, et al., 2012
Welke, J.E.; Manfroi, V.; Zanus, M.; Lazarotto, M.; Zini, C.A., Characterization of the volatile profile of Brazilian merlot wines through comprehensive two dimensional gas chromatography time-of-flight mass spectrometric detection, J. Chromatogr. A, 2012, 1226, 124-139, https://doi.org/10.1016/j.chroma.2012.01.002 . [all data]

Gonzalez-Rios, Suarez-Quiroz, et al., 2007
Gonzalez-Rios, O.; Suarez-Quiroz, M.L.; Boulanger, R.; Barel, M.; Guyot, B.; Guiraud, J.-P.; Schorr-Galindo, S., Impact of ecological post-harvest processing of coffee aroma: II Roasted coffee., J. Food Composition Analysis, 2007, 20, 3-4, 297-307, https://doi.org/10.1016/j.jfca.2006.12.004 . [all data]

Kim. J.H., Ahn, et al., 2004
Kim. J.H.; Ahn, H.J.; Yook, H.S.; Kim, K.S.; Rhee, M.S.; Ryu, G.H.; Byun, M.W., Color, flavor, and sensory characteristics of gamma-irradiated salted and fermented anchovy sauce, Radiation Phys. Chem., 2004, 69, 2, 179-187, https://doi.org/10.1016/S0969-806X(03)00400-6 . [all data]

Finkelstein, Kurbatova, et al., 2002
Finkelstein, E.E.; Kurbatova, S.V.; Kolosova, E.A., Study of biological activity of structure analogies of adamantane, Proc. Samara State Univ., 2002, 26, 4, 121-128. [all data]

Muresan, Eillebrecht, et al., 2000
Muresan, S.; Eillebrecht, M.A.J.L.; de Rijk, T.C.; de Jonge, H.G.; Leguijt, T.; Nijhuis, H.H., Aroma profile development of intermediate chocolate products. I. Volatile constituents of block-milk, Food Chem., 2000, 68, 2, 167-174, https://doi.org/10.1016/S0308-8146(99)00171-5 . [all data]

Chang, Seitz, et al., 1995
Chang, C.-Y.; Seitz, L.M.; Chambers, E., IV, Volatile Flavor Components of Breads Made from Hard Red Winter Wheat and Hard White Winter Wheat, Cereal Chem., 1995, 72, 3, 237-242. [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,liquid	Constant pressure heat capacity of liquid
IE (evaluated)	Recommended ionization energy
P_c	Critical pressure
S°_liquid	Entropy of liquid at standard conditions
T	Temperature
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
T_triple	Triple point temperature
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_rS°	Entropy of reaction at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
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Pyrrole

Data at NIST subscription sites:

Gas phase thermochemistry data

Condensed phase thermochemistry data

Constant pressure heat capacity of liquid

Phase change data

Enthalpy of vaporization

Enthalpy of vaporization

Antoine Equation Parameters

Enthalpy of fusion

Entropy of fusion

Reaction thermochemistry data

Individual Reactions

Free energy of reaction

Gas phase ion energetics data

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

Ion clustering data

Clustering reactions

Free energy of reaction

IR Spectrum

Mass spectrum (electron ionization)

Spectrum

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Additional Data

UV/Visible spectrum

Spectrum

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Credits

Additional Data

Gas Chromatography

Kovats' RI, non-polar column, isothermal

Kovats' RI, polar column, isothermal

Van Den Dool and Kratz RI, non-polar column, temperature ramp

Van Den Dool and Kratz RI, non-polar column, custom temperature program

Van Den Dool and Kratz RI, polar column, temperature ramp

Van Den Dool and Kratz RI, polar column, custom temperature program

Normal alkane RI, non-polar column, temperature ramp

Normal alkane RI, non-polar column, custom temperature program

Normal alkane RI, polar column, temperature ramp

Normal alkane RI, polar column, custom temperature program

References

Notes