Pyrrole

• Formula: C₄H₅N
• Molecular weight: 67.0892
• IUPAC Standard InChI:
  

  InChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H Download the identifier in a file.

• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Ion clustering data
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, "lite" edition (thermophysical and thermochemical data)
• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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
fH°gas	143.2	kJ/mol	N/A	Zaheeruddin and Lodhi, 1991	Value computed using «DELTA»fHliquid° value of 98.0 kj/mol from Zaheeruddin and Lodhi, 1991 and «DELTA»vapH° value of 45.2 kj/mol from Scott, Berg, et al., 1967.; DRB
fH°gas	108.3 ± 0.50	kJ/mol	Ccb	Scott, Berg, et al., 1967	ALS

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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
fH°liquid			Ccb	Zaheeruddin and Lodhi, 1991	uncertain value: 98.02 kJ/mol; ALS
fH°liquid	63.1 ± 0.4	kJ/mol	Ccb	Scott, Berg, et al., 1967	ALS
Quantity	Value	Units	Method	Reference	Comment
cH°liquid			Ccb	Zaheeruddin and Lodhi, 1991	uncertain value: -2386.66 kJ/mol; ALS
cH°liquid	-2351.7 ± 0.3	kJ/mol	Ccb	Scott, Berg, et al., 1967	ALS
cH°liquid	-2350.	kJ/mol	Ccb	Zimmerman and Geisenfelder, 1961	ALS
Quantity	Value	Units	Method	Reference	Comment
S°liquid	156.44	J/mol*K	N/A	Scott, Berg, et al., 1967	DH

Constant pressure heat capacity of liquid

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein 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
Tboil	403. ± 1.	K	AVG	N/A	Average of 15 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Tfus	250.15	K	N/A	Rosso and Carbonnel, 1973	Uncertainty assigned by TRC = 0.6 K; TRC
Tfus	254.7	K	N/A	Timmermans and Hennaut-Roland, 1955	Uncertainty assigned by TRC = 0.5 K; TRC
Tfus	249.7	K	N/A	Anonymous, 1942	Uncertainty assigned by TRC = 0.2 K; TRC
Tfus	238.8	K	N/A	Milazzo, 1941	Uncertainty assigned by TRC = 0.4 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Ttriple	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
Ttriple	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
Ttriple	249.74	K	N/A	McCullough and Waddington, 1957	Uncertainty assigned by TRC = 0.06 K; IPTS-48, from freezing curve; TRC
Ttriple	249.74	K	N/A	McCullough and Waddington, 1957	Uncertainty assigned by TRC = 0.06 K; IPTS-48, from heating curve; TRC
Ttriple	249.75	K	N/A	Anonymous, 1956	Uncertainty assigned by TRC = 0.08 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Tc	639.8	K	N/A	Majer and Svoboda, 1985
Tc	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
Tc	625.15	K	N/A	Glaser and Ruland, 1957	Uncertainty assigned by TRC = 2. K; TRC
Quantity	Value	Units	Method	Reference	Comment
Pc	56.742	bar	N/A	Glaser and Ruland, 1957	Uncertainty assigned by TRC = 3.0398 bar; TRC
Quantity	Value	Units	Method	Reference	Comment
vapH°	43. ± 6.	kJ/mol	AVG	N/A	Average of 6 values; Individual data points

Enthalpy of vaporization

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

Enthalpy of vaporization

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

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K)	A (kJ/mol)		Tc (K)	Reference	Comment
362. - 403.	62.7	0.2964	639.8	Majer and Svoboda, 1985

Antoine Equation Parameters

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

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Enthalpy of fusion

fusH (kJ/mol)	Temperature (K)	Reference	Comment
7.9078	249.74	Scott, Berg, et al., 1967	DH
7.91	249.7	Domalski and Hearing, 1996	AC

Entropy of fusion

fusS (J/mol*K)	Temperature (K)	Reference	Comment
31.66	249.74	Scott, Berg, et al., 1967	DH

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

 +  =

By formula: C₄H₄N^- + H⁺ = C₄H₅N

Quantity	Value	Units	Method	Reference	Comment
rH°	1504.3 ± 1.0	kJ/mol	D-EA	Gianola, Ichino, et al., 2004	gas phase; B
rH°	1500. ± 9.2	kJ/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
rH°	1505. ± 12.	kJ/mol	G+TS	Cumming and Kebarle, 1978	gas phase; B
rH°	1500. ± 21.	kJ/mol	EIAE	Muftakhov, Vasil'ev, et al., 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
rG°	1468. ± 8.4	kJ/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
rG°	1472. ± 8.4	kJ/mol	IMRE	Cumming and Kebarle, 1978	gas phase; B

CN^- +  = (CN^-  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	97.9 ± 4.2	kJ/mol	TDAs	Meot-ner, 1988	gas phase; B,M
rH°	82. ± 15.	kJ/mol	IMRE	Larson and McMahon, 1987	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
rS°	113.	J/mol*K	PHPMS	Meot-ner, 1988	gas phase; M
rS°	99.6	J/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
rG°	64.0 ± 4.2	kJ/mol	TDAs	Meot-ner, 1988	gas phase; B
rG°	51.5 ± 9.6	kJ/mol	IMRE	Larson and McMahon, 1987	gas phase; B,M

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	143. ± 8.4	kJ/mol	IMRE	Larson and McMahon, 1983	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
rS°	107.	J/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
rG°	111. ± 8.4	kJ/mol	IMRE	Larson and McMahon, 1983	gas phase; B,M

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	78.7 ± 8.4	kJ/mol	IMRE	Larson and McMahon, 1984	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
rG°	49.4 ± 8.4	kJ/mol	IMRE	Larson and McMahon, 1984	gas phase; B
rG°	58.58	kJ/mol	TDEq	French, Ikuta, et al., 1982	gas phase; B

Free energy of reaction

rG° (kJ/mol)	T (K)	Method	Reference	Comment
48.5	421.	PHPMS	French, Ikuta, et al., 1982	gas phase; M

HS^- +  = (HS^-  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	96.2 ± 4.2	kJ/mol	TDAs	Meot-ner, 1988	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
rS°	102.	J/mol*K	PHPMS	Meot-ner, 1988	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
rG°	65.7 ± 4.2	kJ/mol	TDAs	Meot-ner, 1988	gas phase; B

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	111. ± 4.2	kJ/mol	TDAs	Meot-ner, 1988, 2	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
rS°	147.	J/mol*K	PHPMS	Meot-ner, 1988, 2	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
rG°	68.2 ± 4.2	kJ/mol	TDAs	Meot-ner, 1988, 2	gas phase; B

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	100. ± 4.2	kJ/mol	TDAs	Meot-ner, 1988	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
rS°	105.	J/mol*K	PHPMS	Meot-ner, 1988	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
rG°	69.0 ± 4.2	kJ/mol	TDAs	Meot-ner, 1988	gas phase; B

(C₄H₅N⁺  ) +  = (C₄H₅N⁺  2)

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

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
rH°	57.7	kJ/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
rS°	122.	J/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

C₄H₅N⁺ +  = (C₄H₅N⁺  )

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

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
rH°	69.0	kJ/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
rS°	84.9	J/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

(C₄H₆N⁺  ) +  = (C₄H₆N⁺  2)

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

Quantity	Value	Units	Method	Reference	Comment
rH°	51.5	kJ/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
rS°	127.	J/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

(  ) +  = (  2)

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

Quantity	Value	Units	Method	Reference	Comment
rH°	71.5	kJ/mol	PHPMS	Meot-ner, 1988, 2	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
rS°	131.	J/mol*K	PHPMS	Meot-ner, 1988, 2	gas phase; M

C₄H₆N⁺ +  = (C₄H₆N⁺  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	70.3	kJ/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
rS°	103.	J/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

(  ) +  = (  2)

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

Quantity	Value	Units	Method	Reference	Comment
rH°	74.9	kJ/mol	PHPMS	Meot-ner, 1988	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
rS°	101.	J/mol*K	PHPMS	Meot-ner, 1988	gas phase; M

CH₆N⁺ +  = (CH₆N⁺  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	77.8	kJ/mol	PHPMS	Deakyne and Meot-Ner (Mautner), 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
rS°	87.9	J/mol*K	PHPMS	Deakyne and Meot-Ner (Mautner), 1985	gas phase; M

 +  = (  )

By formula: C₆H₁₁NO₃ + C₄H₅N = (C₆H₁₁NO₃  C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
rH°	100.	kJ/mol	PHPMS	Meot-Ner (Mautner), 1988	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
rS°	134.	J/mol*K	PHPMS	Meot-Ner (Mautner), 1988	gas phase; M

(  ) +  = (  2)

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

Quantity	Value	Units	Method	Reference	Comment
rH°	174.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

(  ) +  = (  2)

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

Quantity	Value	Units	Method	Reference	Comment
rH°	146.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

(  ) +  = (  2)

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

Quantity	Value	Units	Method	Reference	Comment
rH°	113.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

(  ) +  = (  2)

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

Quantity	Value	Units	Method	Reference	Comment
rH°	197.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

(  ) +  = (  2)

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

Quantity	Value	Units	Method	Reference	Comment
rH°	194.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

(  ) +  = (  2)

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

Quantity	Value	Units	Method	Reference	Comment
rH°	184.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	177. ± 17.	kJ/mol	CIDT	Huang and Rodgers, 2002	RCD

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	102. ± 4.6	kJ/mol	CIDT	Huang and Rodgers, 2002	RCD

 +  = (  )

By formula: K⁺ + C₄H₅N = (K⁺  C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
rH°	83.7 ± 4.2	kJ/mol	CIDT	Huang and Rodgers, 2002	RCD

 +  = (  )

By formula: V⁺ + C₄H₅N = (V⁺  C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
rH°	>170.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	>280.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

 +  = (  )

By formula: W⁺ + C₄H₅N = (W⁺  C₄H₅N)

Quantity	Value	Units	Method	Reference	Comment
rH°	>210.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	>280.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	>290.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	226.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	178.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	177.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	184.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	184.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

 +  = (  )

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

Quantity	Value	Units	Method	Reference	Comment
rH°	247.	kJ/mol	RAK	Gapeev and Yang, 2000	RCD

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

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

• gas

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

Anonymous, 1956
Anonymous, R., , Physical Properties of Chemical Substances, Dow Chemical Company, 1956. [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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  cH°liquid	Enthalpy of combustion of liquid at standard conditions
  fH°gas	Enthalpy of formation of gas at standard conditions
  fH°liquid	Enthalpy of formation of liquid at standard conditions
  fusH	Enthalpy of fusion
  fusS	Entropy of fusion
  rG°	Free energy of reaction at standard conditions
  rH°	Enthalpy of reaction at standard conditions
  rS°	Entropy of reaction at standard conditions
  vapH	Enthalpy of vaporization
  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.
• Customer support for NIST Standard Reference Data products.