Pyridine
- Formula: C5H5N
- Molecular weight: 79.0999
- IUPAC Standard InChIKey: JUJWROOIHBZHMG-UHFFFAOYSA-N
- CAS Registry Number: 110-86-1
- 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. - Isotopologues:
- Other names: Azabenzene; Azine; NCI-C55301; Piridina; Pirydyna; Pyridin; Rcra waste number U196; UN 1282; Pyr; CP 32; NSC 406123
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 33.50 | kcal/mol | Ccb | Hubbard, Frow, et al., 1961 | ALS |
ΔfH°gas | 33.61 ± 0.36 | kcal/mol | Cm | Andon, Cox, et al., 1957 | ALS |
ΔfH°gas | 33.63 ± 0.36 | kcal/mol | Ccb | Cox, Challoner, et al., 1954 | ALS |
ΔfH°gas | 26.31 | kcal/mol | N/A | Constam and White, 1903 | Value computed using ΔfHliquid° value of 69.9 kj/mol from Constam and White, 1903 and ΔvapH° value of 40.2 kj/mol from Hubbard, Frow, et al., 1961.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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 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 |
---|---|---|---|---|---|
ΔfH°liquid | 23.89 ± 0.12 | kcal/mol | Ccb | Hubbard, Frow, et al., 1961 | ALS |
ΔfH°liquid | 23.95 ± 0.36 | kcal/mol | Ccb | Cox, Challoner, et al., 1954 | ALS |
ΔfH°liquid | 16.7 | kcal/mol | Ccb | Constam and White, 1903 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -651.3 | kcal/mol | Ccb | Strepikheev, Baranov, et al., 1962 | ALS |
ΔcH°liquid | -664.95 ± 0.10 | kcal/mol | Ccb | Hubbard, Frow, et al., 1961 | ALS |
ΔcH°liquid | -665.00 ± 0.36 | kcal/mol | Ccb | Cox, Challoner, et al., 1954 | ALS |
ΔcH°liquid | -659.2 | kcal/mol | Ccb | Constam and White, 1903 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 42.519 | cal/mol*K | N/A | McCullough, Douslin, et al., 1957 | DH |
S°liquid | 42.81 | cal/mol*K | N/A | Parks, Todd, et al., 1936 | Extrapolation below 90 K, 50.04 J/mol*K.; DH |
S°liquid | 50.289 | cal/mol*K | N/A | Pearce and Bakke, 1936 | Extrapolation below 90 K, 89.33 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
46.22 | 293. | Rastorguev and Ganiev, 1967 | T = 293 to 353 K.; DH |
31.8 | 298.15 | Hubbard, Frow, et al., 1961 | DH |
35.11 | 332. | Swietoslawski and Zielenkiewicz, 1958 | Mean value 22 to 96°C.; DH |
31.721 | 298.15 | McCullough, Douslin, et al., 1957 | T = 10 to 350 K.; DH |
32.249 | 298.1 | Parks, Todd, et al., 1936 | T = 90 to 300 K.; DH |
31.859 | 298.1 | Pearce and Bakke, 1936 | T = 90 to 298 K. Value is unsmoothed experimental datum.; DH |
30.90 | 289. | Radulescu and Jula, 1934 | DH |
32.349 | 273.4 | Swietoslawski, Tybicka, et al., 1931 | DH |
32.41 | 290. | Swietoslawski, Tybicka, et al., 1931, 2 | DH |
30.911 | 294. | Mathews, Krause, et al., 1917 | DH |
31.19 | 283. | Bramley, 1916 | Mean value, 0 to 20°C.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 388.5 ± 0.6 | K | AVG | N/A | Average of 80 out of 84 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 232. ± 2. | K | AVG | N/A | Average of 26 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 231.48 | K | N/A | Helm, Lanum, et al., 1958 | Uncertainty assigned by TRC = 0.03 K; measured in calorimeter at USBM, Bartlesville, OK; TRC |
Ttriple | 231.480 | K | N/A | McCullough, Douslin, et al., 1957, 2 | Uncertainty assigned by TRC = 0.05 K; by extrapolation of 1/f to zero; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 619. ± 2. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 55.86 | atm | N/A | Brunner, 1987 | Uncertainty assigned by TRC = 0.0558 atm; Visual, optical cell 30cm high. P transducer cal. vs PB.; TRC |
Pc | 55.66 | atm | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 1.020 atm; TRC |
Pc | 60.000 | atm | N/A | Herz and Neukirch, 1923 | Uncertainty assigned by TRC = 0.8000 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.253 | l/mol | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 0.005 l/mol; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.63 ± 0.06 | kcal/mol | AVG | N/A | Average of 10 out of 11 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.387 | 388.4 | N/A | Majer and Svoboda, 1985 | |
9.39 | 324. | N/A | Ukraintseva, Soldatov, et al., 1997 | Based on data from 289. to 358. K.; AC |
8.99 | 354. | N/A | Blanco, Beltran, et al., 1994 | Based on data from 346. to 362. K.; AC |
9.54 | 310. | EB | Lencka, 1990 | Based on data from 295. to 388. K.; AC |
9.49 | 311. | A | Stephenson and Malanowski, 1987 | Based on data from 296. to 353. K.; AC |
8.91 | 363. | A | Stephenson and Malanowski, 1987 | Based on data from 348. to 434. K.; AC |
8.37 | 446. | A | Stephenson and Malanowski, 1987 | Based on data from 431. to 558. K.; AC |
8.13 | 567. | A | Stephenson and Malanowski, 1987 | Based on data from 552. to 620. K.; AC |
8.99 | 355. | EB | Stephenson and Malanowski, 1987 | Based on data from 340. to 426. K. See also McCullough, Douslin, et al., 1957.; AC |
9.46 | 313. | C | Michou-Saucet, Jose, et al., 1986 | Based on data from 298. to 333. K.; AC |
9.42 | 313. | C | Majer, Svoboda, et al., 1984 | AC |
9.20 | 328. | C | Majer, Svoboda, et al., 1984 | AC |
9.01 | 343. | C | Majer, Svoboda, et al., 1984 | AC |
8.68 | 368. | N/A | Majer, Svoboda, et al., 1984 | AC |
8.96 ± 0.02 | 346. | C | McCullough, Douslin, et al., 1957 | AC |
8.70 ± 0.02 | 366. | C | McCullough, Douslin, et al., 1957 | AC |
8.39 ± 0.02 | 388. | C | McCullough, Douslin, et al., 1957 | AC |
9.18 | 335. | MG | Herington and Martin, 1953 | Based on data from 320. to 388. K.; AC |
10.6 | 273. | N/A | Meulen and Mann, 1931 | Based on data from 258. to 389. K.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 388. | 13.25 | 0.2536 | 620. | 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 |
---|---|---|---|---|---|
340.5 to 426.04 | 4.15701 | 1371.358 | -58.496 | McCullough, Douslin, et al., 1957 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.9786 | 231.49 | McCullough, Douslin, et al., 1957 | Includes energy of anomaly at about 210 K.; DH |
1.98 | 231.5 | Domalski and Hearing, 1996 | AC |
1.977 | 231.1 | Parks, Todd, et al., 1936 | DH |
0.7409 | 230.38 | Pearce and Bakke, 1936 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.547 | 231.49 | McCullough, Douslin, et al., 1957 | Includes; DH |
8.554 | 231.1 | Parks, Todd, et al., 1936 | DH |
3.217 | 230.38 | Pearce and Bakke, 1936 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
C5H4N- + =
By formula: C5H4N- + H+ = C5H5N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 389.9 ± 2.0 | kcal/mol | IMRE | Schafman and Wenthold, 2007 | gas phase; B |
ΔrH° | 391.0 ± 2.5 | kcal/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 382.7 ± 2.0 | kcal/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
ΔrG° | 384.0 ± 3.0 | kcal/mol | IMRB | DePuy, Kass, et al., 1988 | gas phase; Comparable to water in acidity; B |
ΔrG° | <376.3 ± 2.0 | kcal/mol | IMRB | Bruins, Ferrer-Correia, et al., 1978 | gas phase; O- deprotonates; B |
By formula: C5H6N+ + C5H5N = (C5H6N+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 25.2 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 24.6 | kcal/mol | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase; M |
ΔrH° | 26.3 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
ΔrH° | 23.7 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
ΔrH° | 23.7 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.6 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 28.2 | cal/mol*K | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase; M |
ΔrS° | 32.1 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
ΔrS° | 28. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
ΔrS° | 28. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
By formula: C5H5N + 3H2 = C5H11N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -46.31 ± 0.18 | kcal/mol | Eqk | Hales and Herington, 1957 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -48.32 ± 0.18 kcal/mol; At 400-550 K; ALS |
ΔrH° | -46.12 ± 0.50 | kcal/mol | Eqk | Burrows and King, 1935 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -45.00 kcal/mol; At 423-443 K; ALS |
By formula: Cl- + C5H5N = (Cl- • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.7 ± 2.0 | kcal/mol | TDAs | Hiraoka, Mizuse, et al., 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 19.7 | cal/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 6.8 ± 2.6 | kcal/mol | TDAs | Hiraoka, Mizuse, et al., 1988 | gas phase; B |
By formula: (C5H6N+ • 2C5H5N) + C5H5N = (C5H6N+ • 3C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 13.6 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 37.9 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
By formula: Li+ + C5H5N = (Li+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 43.2 ± 3.5 | kcal/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
ΔrH° | 44. | kcal/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M |
By formula: K+ + C5H5N = (K+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 21.6 ± 0.9 | kcal/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
ΔrH° | 20.7 | kcal/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 18.6 | cal/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
By formula: (Ag+ • 2C5H5N) + C5H5N = (Ag+ • 3C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 16.7 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28.0 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: (Ag+ • 3C5H5N) + C5H5N = (Ag+ • 4C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 17.9 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 40.3 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: (Cl- • C5H5N) + C5H5N = (Cl- • 2C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 11.7 | kcal/mol | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22.6 | cal/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
By formula: (C5H6N+ • C5H5N) + C5H5N = (C5H6N+ • 2C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.6 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.7 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: H2O3- + C5H5N + H2O = C5H7NO3-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 32.7 ± 2.3 | kcal/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
+
= C5H5NO2-
By formula: O2- + C5H5N = C5H5NO2-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 21.7 ± 2.3 | kcal/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
+
= C5H5N2O-
By formula: NO- + C5H5N = C5H5N2O-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 13.6 ± 2.3 | kcal/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
3 +
= 3
+ KClO3
By formula: 3C5H5NO + ClK = 3C5H5N + KClO3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 75.2 ± 2.4 | kcal/mol | Cm | Shaofeng and Pilcher, 1988 | solid phase; ALS |
3 +
= 3
+ KBrO3
By formula: 3C5H5NO + BrK = 3C5H5N + KBrO3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 75.0 ± 2.3 | kcal/mol | Cm | Shaofeng and Pilcher, 1988 | solid phase; ALS |
By formula: Fe+ + C5H5N = (Fe+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 53.4 ± 2.2 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Cr+ + C5H5N = (Cr+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 47.1 ± 2.8 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Ti+ + C5H5N = (Ti+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 51.9 ± 2.3 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Mn+ + C5H5N = (Mn+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 43.4 ± 2.1 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Sc+ + C5H5N = (Sc+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 55.3 ± 2.5 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Mg+ + C5H5N = (Mg+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 47.8 ± 1.6 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: V+ + C5H5N = (V+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 52.2 ± 3.2 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Ni+ + C5H5N = (Ni+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 60.9 ± 3.7 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Al+ + C5H5N = (Al+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 45.5 ± 2.5 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Zn+ + C5H5N = (Zn+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 59.0 ± 1.7 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Co+ + C5H5N = (Co+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 59.0 ± 3.0 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Cu+ + C5H5N = (Cu+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 58.7 ± 2.5 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Na+ + C5H5N = (Na+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 30.3 ± 0.7 | kcal/mol | CIDT | Amunugama and Rodgers, 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, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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
MM - Michael M. Meot-Ner (Mautner)
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) | 9.26 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 222. | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 214.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
223.8 ± 2.0 | Wind, Papp, et al., 2005 | T = 298K; MM |
Protonation entropy at 298K
Protonation entropy (cal/mol*K) | Reference | Comment |
---|---|---|
-0.2 ± 2.4 | Wind, Papp, et al., 2005 | T = 298K; MM |
Ionization energy determinations
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H3+ | 14.00 ± 0.10 | ? | EI | Momigny, Urbain, et al., 1965 | RDSH |
C3H3N+ | 13.84 ± 0.10 | C2H2 | EI | Momigny, Urbain, et al., 1965 | RDSH |
C4H2+ | 16.17 ± 0.10 | HCN+H2 | EI | Momigny, Urbain, et al., 1965 | RDSH |
C4H3+ | 16.61 ± 0.10 | HCN+H | EI | Momigny, Urbain, et al., 1965 | RDSH |
C4H4+ | 11.84 ± 0.05 | HCN | TRPI | Lifshitz and Malinovich, 1984 | LBLHLM |
C4H4+ | 12.6 ± 0.1 | HCN | EI | Burgers and Holmes, 1984 | LBLHLM |
C4H4+ | 12.34 ± 0.05 | HCN | EI | Burgers and Holmes, 1984 | LBLHLM |
C4H4+ | 12.0 ± 0.2 | HCN | TRPI | Lifshitz, 1982 | LBLHLM |
C4H4+ | 12.15 ± 0.02 | HCN | PIPECO | Rosenstock, Stockbauer, et al., 1981 | LLK |
C4H4+ | 11.8 | HCN | PI | Eland, Berkowitz, et al., 1978 | LLK |
C4H4+ | 12.3 ± 0.1 | HCN | EI | Rosenstock, McCulloh, et al., 1977 | LLK |
C4H4+ | 13.41 ± 0.05 | HCN | EI | Zaretskii, Oren, et al., 1976 | LLK |
C4H4+ | 13.28 | HCN | EI | Beynon, Hopkinson, et al., 1969 | RDSH |
C5H3N+ | 12.42 ± 0.10 | H2 | EI | Momigny, Urbain, et al., 1965 | RDSH |
C5H4N+ | 14.00 ± 0.10 | H | EI | Momigny, Urbain, et al., 1965 | RDSH |
De-protonation reactions
C5H4N- + =
By formula: C5H4N- + H+ = C5H5N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 389.9 ± 2.0 | kcal/mol | IMRE | Schafman and Wenthold, 2007 | gas phase; B |
ΔrH° | 391.0 ± 2.5 | kcal/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 382.7 ± 2.0 | kcal/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
ΔrG° | 384.0 ± 3.0 | kcal/mol | IMRB | DePuy, Kass, et al., 1988 | gas phase; Comparable to water in acidity; B |
ΔrG° | <376.3 ± 2.0 | kcal/mol | IMRB | Bruins, Ferrer-Correia, et al., 1978 | gas phase; O- deprotonates; B |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
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
By formula: (Ag+ • 2C5H5N) + C5H5N = (Ag+ • 3C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 16.7 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28.0 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: (Ag+ • 3C5H5N) + C5H5N = (Ag+ • 4C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 17.9 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 40.3 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: Al+ + C5H5N = (Al+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 45.5 ± 2.5 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: C5H6N+ + C5H5N = (C5H6N+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 25.2 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 24.6 | kcal/mol | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase; M |
ΔrH° | 26.3 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
ΔrH° | 23.7 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
ΔrH° | 23.7 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.6 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 28.2 | cal/mol*K | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase; M |
ΔrS° | 32.1 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
ΔrS° | 28. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
ΔrS° | 28. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
By formula: (C5H6N+ • C5H5N) + C5H5N = (C5H6N+ • 2C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.6 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.7 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: (C5H6N+ • 2C5H5N) + C5H5N = (C5H6N+ • 3C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 13.6 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 37.9 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
By formula: Cl- + C5H5N = (Cl- • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.7 ± 2.0 | kcal/mol | TDAs | Hiraoka, Mizuse, et al., 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 19.7 | cal/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 6.8 ± 2.6 | kcal/mol | TDAs | Hiraoka, Mizuse, et al., 1988 | gas phase; B |
By formula: (Cl- • C5H5N) + C5H5N = (Cl- • 2C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 11.7 | kcal/mol | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22.6 | cal/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
By formula: Co+ + C5H5N = (Co+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 59.0 ± 3.0 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Cr+ + C5H5N = (Cr+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 47.1 ± 2.8 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Cu+ + C5H5N = (Cu+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 58.7 ± 2.5 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Fe+ + C5H5N = (Fe+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 53.4 ± 2.2 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: H2O3- + C5H5N + H2O = C5H7NO3-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 32.7 ± 2.3 | kcal/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
By formula: K+ + C5H5N = (K+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 21.6 ± 0.9 | kcal/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
ΔrH° | 20.7 | kcal/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 18.6 | cal/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
By formula: Li+ + C5H5N = (Li+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 43.2 ± 3.5 | kcal/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
ΔrH° | 44. | kcal/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M |
By formula: Mg+ + C5H5N = (Mg+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 47.8 ± 1.6 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Mn+ + C5H5N = (Mn+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 43.4 ± 2.1 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
+
= C5H5N2O-
By formula: NO- + C5H5N = C5H5N2O-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 13.6 ± 2.3 | kcal/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
By formula: Na+ + C5H5N = (Na+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 30.3 ± 0.7 | kcal/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
By formula: Ni+ + C5H5N = (Ni+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 60.9 ± 3.7 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
+
= C5H5NO2-
By formula: O2- + C5H5N = C5H5NO2-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 21.7 ± 2.3 | kcal/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
By formula: Sc+ + C5H5N = (Sc+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 55.3 ± 2.5 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Ti+ + C5H5N = (Ti+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 51.9 ± 2.3 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: V+ + C5H5N = (V+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 52.2 ± 3.2 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Zn+ + C5H5N = (Zn+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 59.0 ± 1.7 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
IR Spectrum
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, References, Notes
Data compiled by: Coblentz Society, Inc.
- GAS (15 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 3800-1300, 10% IN CS2 FOR 1300-650, 10% IN CCl4 FOR 650-250 CM-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- VAPOR (0.5 MICROLITER AT 150 C); NICOLET FTIR; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 CM-1 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Hubbard, Frow, et al., 1961
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The heats of combustion and formation of pyridine and hippuric acid,
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Meulen, P.A. van der.; Mann, Russell F.,
THE VAPOR PRESSURE OF PYRIDINE,
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Schafman and Wenthold, 2007
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Regioselectivity of pyridine deprotonation in the gas phase,
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Meot-ner and Kafafi, 1988
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Carbon Acidities of Aromatic Compounds,
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Kiefer, Zhang, et al., 1997
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Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine,
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DePuy, Kass, et al., 1988
DePuy, C.H.; Kass, S.R.; Bean, G.P.,
Formation and Reactions of Heteroaromatic Anions in the Gas Phase,
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Bruins, Ferrer-Correia, et al., 1978
Bruins, A.P.; Ferrer-Correia, A.J.; Harrison, A.G.; Jennings, K.R.; Mithcum, R.K.,
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Meot-Ner (Mautner), 1992
Meot-Ner (Mautner), M.,
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Meot-Ner M. and Sieck, 1983
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Meot-Ner (Mautner), 1979
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Hales and Herington, 1957
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Equilibrium between pyridine and piperidine,
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Burrows and King, 1935
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The free energy change that accompanies hydrogenation of pyridine to piperidine,
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Hiraoka, Mizuse, et al., 1988
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Determination of the Stabilities and Structures of X-(C6H6) Clusters (X = Cl, Br, and I),
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Absolute Alkali Metal Ion Binding Affinities of Several Azines Determined by Threshold Collision-Induced Dissociation and Ab Initio Theory,
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Notes
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- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Vc Critical volume ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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