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, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 | 140.2 | kJ/mol | Ccb | Hubbard, Frow, et al., 1961 | ALS |
ΔfH°gas | 140.6 ± 1.5 | kJ/mol | Cm | Andon, Cox, et al., 1957 | ALS |
ΔfH°gas | 140.7 ± 1.5 | kJ/mol | Ccb | Cox, Challoner, et al., 1954 | ALS |
ΔfH°gas | 110.1 | kJ/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 |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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° | 1631. ± 8.4 | kJ/mol | IMRE | Schafman and Wenthold, 2007 | gas phase; B |
ΔrH° | 1636. ± 10. | kJ/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° | 1601. ± 8.4 | kJ/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° | 1607. ± 13. | kJ/mol | IMRB | DePuy, Kass, et al., 1988 | gas phase; Comparable to water in acidity; B |
ΔrG° | <1574. ± 8.4 | kJ/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° | 105. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 103. | kJ/mol | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase; M |
ΔrH° | 110. | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
ΔrH° | 99.2 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
ΔrH° | 99.2 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 124. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 118. | J/mol*K | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase; M |
ΔrS° | 134. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
ΔrS° | 120. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
ΔrS° | 120. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
By formula: C5H5N + 3H2 = C5H11N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -193.8 ± 0.75 | kJ/mol | Eqk | Hales and Herington, 1957 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -202.2 ± 0.75 kJ/mol; At 400-550 K; ALS |
ΔrH° | -193.0 ± 2.1 | kJ/mol | Eqk | Burrows and King, 1935 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -188.3 kJ/mol; At 423-443 K; ALS |
By formula: Cl- + C5H5N = (Cl- • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 53.1 ± 8.4 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 82.4 | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 28. ± 11. | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1988 | gas phase; B |
By formula: (C5H6N+ • 2C5H5N) + C5H5N = (C5H6N+ • 3C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 56.9 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 159. | J/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° | 181. ± 15. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
ΔrH° | 180. | kJ/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° | 90. ± 4. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
ΔrH° | 86.6 | kJ/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 77.8 | J/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
By formula: (Ag+ • 2C5H5N) + C5H5N = (Ag+ • 3C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 69.9 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 117. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: (Ag+ • 3C5H5N) + C5H5N = (Ag+ • 4C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 74.9 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 169. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: (Cl- • C5H5N) + C5H5N = (Cl- • 2C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 49.0 | kJ/mol | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 94.6 | J/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° | 52.7 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 124. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: H2O3- + C5H5N + H2O = C5H7NO3-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 137. ± 9.6 | kJ/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° | 90.8 ± 9.6 | kJ/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° | 56.9 ± 9.6 | kJ/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° | 315. ± 10. | kJ/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° | 313.6 ± 9.6 | kJ/mol | Cm | Shaofeng and Pilcher, 1988 | solid phase; ALS |
By formula: Fe+ + C5H5N = (Fe+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 223. ± 9.2 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Cr+ + C5H5N = (Cr+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 197. ± 12. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Ti+ + C5H5N = (Ti+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 217. ± 9.6 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Mn+ + C5H5N = (Mn+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 182. ± 8.8 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Sc+ + C5H5N = (Sc+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 231. ± 10. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Mg+ + C5H5N = (Mg+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 200. ± 6.7 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: V+ + C5H5N = (V+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 218. ± 13. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Ni+ + C5H5N = (Ni+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 255. ± 15. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Al+ + C5H5N = (Al+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 190. ± 10. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Zn+ + C5H5N = (Zn+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 247. ± 7.1 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Co+ + C5H5N = (Co+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 247. ± 13. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Cu+ + C5H5N = (Cu+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 246. ± 10. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Na+ + C5H5N = (Na+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 127. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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) | 930. | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 898.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
936.5 ± 8.5 | Wind, Papp, et al., 2005 | T = 298K; MM |
Protonation entropy at 298K
Protonation entropy (J/mol*K) | Reference | Comment |
---|---|---|
-1. ± 10. | 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° | 1631. ± 8.4 | kJ/mol | IMRE | Schafman and Wenthold, 2007 | gas phase; B |
ΔrH° | 1636. ± 10. | kJ/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° | 1601. ± 8.4 | kJ/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° | 1607. ± 13. | kJ/mol | IMRB | DePuy, Kass, et al., 1988 | gas phase; Comparable to water in acidity; B |
ΔrG° | <1574. ± 8.4 | kJ/mol | IMRB | Bruins, Ferrer-Correia, et al., 1978 | gas phase; O- deprotonates; B |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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° | 69.9 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 117. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: (Ag+ • 3C5H5N) + C5H5N = (Ag+ • 4C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 74.9 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 169. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: Al+ + C5H5N = (Al+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 190. ± 10. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: C5H6N+ + C5H5N = (C5H6N+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 105. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 103. | kJ/mol | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase; M |
ΔrH° | 110. | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
ΔrH° | 99.2 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
ΔrH° | 99.2 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 124. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 118. | J/mol*K | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase; M |
ΔrS° | 134. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
ΔrS° | 120. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
ΔrS° | 120. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
By formula: (C5H6N+ • C5H5N) + C5H5N = (C5H6N+ • 2C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 52.7 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 124. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: (C5H6N+ • 2C5H5N) + C5H5N = (C5H6N+ • 3C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 56.9 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 159. | J/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° | 53.1 ± 8.4 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 82.4 | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 28. ± 11. | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1988 | gas phase; B |
By formula: (Cl- • C5H5N) + C5H5N = (Cl- • 2C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 49.0 | kJ/mol | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 94.6 | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
By formula: Co+ + C5H5N = (Co+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 247. ± 13. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Cr+ + C5H5N = (Cr+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 197. ± 12. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Cu+ + C5H5N = (Cu+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 246. ± 10. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Fe+ + C5H5N = (Fe+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 223. ± 9.2 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: H2O3- + C5H5N + H2O = C5H7NO3-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 137. ± 9.6 | kJ/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° | 90. ± 4. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
ΔrH° | 86.6 | kJ/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 77.8 | J/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
By formula: Li+ + C5H5N = (Li+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 181. ± 15. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
ΔrH° | 180. | kJ/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° | 200. ± 6.7 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Mn+ + C5H5N = (Mn+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 182. ± 8.8 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
+
= C5H5N2O-
By formula: NO- + C5H5N = C5H5N2O-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 56.9 ± 9.6 | kJ/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° | 127. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
By formula: Ni+ + C5H5N = (Ni+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 255. ± 15. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
+
= C5H5NO2-
By formula: O2- + C5H5N = C5H5NO2-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 90.8 ± 9.6 | kJ/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° | 231. ± 10. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Ti+ + C5H5N = (Ti+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 217. ± 9.6 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: V+ + C5H5N = (V+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 218. ± 13. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Zn+ + C5H5N = (Zn+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 247. ± 7.1 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), UV/Visible spectrum, 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
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible 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.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | Japan AIST/NIMC Database- Spectrum MS-NW- 79 |
NIST MS number | 227742 |
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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 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
View image of digitized spectrum (can be printed in landscape orientation).
View spectrum image in SVG format.
Download spectrum in JCAMP-DX format.
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. 1112 |
Instrument | Zeiss PMQII |
Melting point | -41.6 |
Boiling point | 115.2 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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
Hubbard, W.N.; Frow, F.R.; Waddington, G.,
The heats of combustion and formation of pyridine and hippuric acid,
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Andon, Cox, et al., 1957
Andon, R.J.L.; Cox, J.D.; Herington, E.F.G.; Martin, J.F.,
The second virial coefficients of pyridine and benzene, and certain of their methyl homologues,
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Cox, Challoner, et al., 1954
Cox, J.D.; Challoner, A.R.; Meetham, A.R.,
The heats of combustion of pyridine and certain of its derivatives,
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Constam and White, 1903
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Physico-chemical investigations in the pyridine series,
Am. Chem. J., 1903, 29, 1-49. [all data]
Schafman and Wenthold, 2007
Schafman, B.S.; Wenthold, P.G.,
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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DePuy, C.H.; Kass, S.R.; Bean, G.P.,
Formation and Reactions of Heteroaromatic Anions in the Gas Phase,
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Bruins, A.P.; Ferrer-Correia, A.J.; Harrison, A.G.; Jennings, K.R.; Mithcum, R.K.,
Negative ion chemical ionization mass spectrometry of some aromatic compounds using O-. as the reagent ion,
Adv. Mass Spectrom., 1978, 7, 355. [all data]
Meot-Ner (Mautner), 1992
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Intermolecular Forces in Organic Clusters,
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The Ionic Hydrogen Bond. 1. Sterically Hindered Bonds. Solvation and Clustering of Sterically Hindered Amines and Pyridines,
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Holland and Castleman, 1982
Holland, P.M.; Castleman, A.W.,
The Thermochemical Properties of Gas - Phase Transition Metal Ion Complexes,
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Meot-Ner (Mautner), 1979
Meot-Ner (Mautner), M.,
Ion Thermochemistry of Low Volatility Compounds in the Gas Phase. II. Intrinsic Basicities and Hydrogen Bonded Dimers of Nitrogen Heterocyclics and Nucleic Bases,
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. [all data]
Hales and Herington, 1957
Hales, J.L.; Herington, E.F.G.,
Equilibrium between pyridine and piperidine,
Trans. Faraday Soc., 1957, 53, 616-622. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Burrows and King, 1935
Burrows, G.H.; King, L.A., Jr.,
The free energy change that accompanies hydrogenation of pyridine to piperidine,
J. Am. Chem. Soc., 1935, 57, 1789-1791. [all data]
Hiraoka, Mizuse, et al., 1988
Hiraoka, K.; Mizuse, S.; Yamabe, S.,
Determination of the Stabilities and Structures of X-(C6H6) Clusters (X = Cl, Br, and I),
Chem. Phys. Lett., 1988, 147, 2-3, 174, https://doi.org/10.1016/0009-2614(88)85078-4
. [all data]
Amunugama and Rodgers, 2000
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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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. [all data]
Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L.,
Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases,
J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050
. [all data]
Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P.,
Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n,
J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013
. [all data]
Davidson and Kebarle, 1976
Davidson, W.R.; Kebarle, P.,
Binding Energies and Stabilities of Potassium Ion Complexes from Studies of Gas Phase Ion Equilibria K+ + M = K+.M,
J. Am. Chem. Soc., 1976, 98, 20, 6133, https://doi.org/10.1021/ja00436a011
. [all data]
Le Barbu, Schiedt, et al., 2002
Le Barbu, K.; Schiedt, J.; Weinkauf, R.; Schlag, E.W.; Nilles, J.M.; Xu, S.J.; Thomas, O.C.; Bowen, K.H.,
Microsolvation of small anions by aromatic molecules: An exploratory study,
J. Chem. Phys., 2002, 116, 22, 9663-9671, https://doi.org/10.1063/1.1475750
. [all data]
Shaofeng and Pilcher, 1988
Shaofeng, L.; Pilcher, G.,
Enthalpy of formation of pyridine-N-oxide: the dissociation enthalpy of the (N-O) bond,
J. Chem. Thermodyn., 1988, 20, 463-465. [all data]
Rodgers, Stanley, et al., 2000
Rodgers, M.T.; Stanley, J.R.; Amunugama, R.,
Periodic Trends in the Binding of Metal Ions to Pyridine Studied by Threshold Collision-Induced Dissociation and Density Functional Theory,
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. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
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. [all data]
Wind, Papp, et al., 2005
Wind, J.J.; Papp, L.; Happel, M.; Hahn, K.; Andriole, E.J.; Poutsma, J.C.,
Proton Affinity of beta-Oxalylaminoalanine (BOAA): Incorporation of Direct Entropy Correction into the Single-Reference Kinetic Method,
J. Am. Soc. Mass Spectrom., 2005, 16, 1151. [all data]
Arimura and Yoshikawa, 1984
Arimura, M.; Yoshikawa, Y.,
Ionization efficiency and ionization energy of cyclic compounds by electron impact,
Mass Spectrosc. (Tokyo), 1984, 32, 375. [all data]
Lifshitz, 1982
Lifshitz, C.,
Time-dependent mass spectra and breakdown graphs. 2. The kinetic shift in pyridine,
J. Phys. Chem., 1982, 86, 606. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Utsunomiya, Kobayashi, et al., 1978
Utsunomiya, C.; Kobayashi, T.; Nagakura, S.,
Photoelectron angular distribution measurements for some pyridines,
Bull. Chem. Soc. Jpn., 1978, 451, 3482. [all data]
Eland, Berkowitz, et al., 1978
Eland, J.H.D.; Berkowitz, J.; Schulte, H.; Frey, R.,
Rates of unimolecular pyridine ion decay and the heat of formation of C4H4+,
Int. J. Mass Spectrom. Ion Phys., 1978, 28, 297. [all data]
Zaretskii, Oren, et al., 1976
Zaretskii, Z.V.I.; Oren, D.; Kelner, L.,
Automatic method for the measurement of the electron impact ionization and appearance potentials,
Appl. Spectrosc., 1976, 30, 366. [all data]
Van Veen and Plantenga, 1975
Van Veen, E.H.; Plantenga, F.L.,
Threshold electron-impact excitation spectrum of pyridine,
Chem. Phys. Lett., 1975, 30, 28. [all data]
Stefanovic and Grutzmacher, 1974
Stefanovic, D.; Grutzmacher, H.F.,
The ionisation potential of some substituted pyridines,
Org. Mass Spectrom., 1974, 9, 1052. [all data]
King, Murrell, et al., 1972
King, G.H.; Murrell, J.N.; Suffolk, R.J.,
The vacuum-ultraviolet photoelectron spectra of fluoropyridines,
J. Chem. Soc. Dalton Trans., 1972, 564. [all data]
Johnstone and Mellon, 1972
Johnstone, R.A.W.; Mellon, F.A.,
Electron-impact ionization and appearance potentials,
J. Chem. Soc. Faraday Trans. 2, 1972, 68, 1209. [all data]
Distefano, Foffani, et al., 1971
Distefano, G.; Foffani, A.; Innorta, G.; Pignataro, S.,
Mass spectrometric study of transition metal complexes with ligands having nitrogen or sulphur as donor atom,
Adv. Mass Spectrom., 1971, 5, 696. [all data]
Distefano, Foffani, et al., 1971, 2
Distefano, G.; Foffani, A.; Innorta, G.; Pignataro, S.,
Electron impact ionization potentials of some manganese, chromium and tungsten organometallic derivatives,
Int. J. Mass Spectrom. Ion Phys., 1971, 7, 383. [all data]
Potapov and Sorokin, 1970
Potapov, V.K.; Sorokin, V.V.,
Investigation of ionic molecular reactions proceeding during photoionization of aromatic compounds and alcohols,
Dokl. Akad. Nauk SSSR, 1970, 195, 616, In original 848. [all data]
Goffart, Momigny, et al., 1969
Goffart, C.; Momigny, J.; Natalis, P.,
Photoionization studies by total ionization measurements and photoelectron spectra. II.Pyridine,
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Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. II.The ionization potentials of azabenzenes and azanaphthalenes,
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Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W.,
Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials,
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Akopyan and Vilesov, 1964
Akopyan, M.E.; Vilesov, F.I.,
Excited states of positive ions and dissociative photoionization of aromatic amines,
Dokl. Akad. Nauk SSSR, 1964, 158, 1386, In original 965. [all data]
Terenin, 1961
Terenin, A.,
Charge transfer in organic solids, induced by light,
Proc. Chem. Soc., London, 1961, 321. [all data]
El-Sayed, Kaaba, et al., 1961
El-Sayed, M.F.A.; Kaaba, M.; Tanaka, Y.,
Ionization potentials of benzene, hexadeuterobenzene, and pyridine from their observed Rydberg series in the region 600-2000 A,
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Watanabe, 1957
Watanabe, K.,
Ionization potentials of some molecules,
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Hustrulid, Kusch, et al., 1938
Hustrulid, A.; Kusch, P.; Tate, J.T.,
The dissociation of benzene (C6H6), pyridine (C5H5N) and cyclohexane (C6H12) by electron impact,
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Klasinc, Novak, et al., 1978
Klasinc, L.; Novak, I.; Scholz, M.; Kluge, G.,
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Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of aminopyridines and cyanopyridines,
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Batich, Heilbronner, et al., 1973
Batich, C.; Heilbronner, E.; Hornung, V.; Ashe, A.J.; Clark, D.T.; Cobley, U.T.; Kilcast, D.; Scanlan, I.,
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Heilbronner, Hornung, et al., 1972
Heilbronner, E.; Hornung, V.; Pinkerton, F.H.; Thames, S.F.,
31. Photoelectron spectra of azabenzenes and azanaphthalenes: III. The orbital sequence in methyl- and trimethylsilyl- substituted pyridines,
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Gleiter, Heilbronner, et al., 1970
Gleiter, R.; Heilbronner, E.; Hornung, V.,
Lone pair interaction in pyridazine, pyrimidine, and pyrazine,
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Momigny, Urbain, et al., 1965
Momigny, J.; Urbain, J.; Wankenne, H.,
Les effets de l'impact electronique sur la pyridine et les diazines isomeres,
Bull. Soc. Roy. Sci. Liege, 1965, 34, 337. [all data]
Lifshitz and Malinovich, 1984
Lifshitz, C.; Malinovich, Y.,
Time resolved photoionization mass spectrometry in the millisecond range,
Int. J. Mass Spectrom. Ion Processes, 1984, 60, 99. [all data]
Burgers and Holmes, 1984
Burgers, P.C.; Holmes, J.L.,
Fragmentation rate constants and appearance energies for reactions having a large kinetic shift and the energy partitioning in their metastable decomposition,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 15. [all data]
Rosenstock, Stockbauer, et al., 1981
Rosenstock, H.M.; Stockbauer, R.; Parr, A.C.,
Unimolecular kinetis of pyridine ion fragmentation,
Int. J. Mass Spectrom. Ion Phys., 1981, 38, 323. [all data]
Rosenstock, McCulloh, et al., 1977
Rosenstock, H.M.; McCulloh, K.E.; Lossing, F.P.,
On the mechanisms of C6H6 ionization fragmentation,
Int. J. Mass Spectrom. Ion Phys., 1977, 25, 327. [all data]
Beynon, Hopkinson, et al., 1969
Beynon, J.H.; Hopkinson, J.A.; Lester, G.R.,
Mass spectrometry-the appearance potentials of "meta-stable peaks" in some aromatic nitro compounds - a chemical reaction in the mass spectrometer,
Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 291. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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