p-pyridinide anion
- Formula: C5H4N-
- Molecular weight: 78.0925
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Reaction thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: John E. Bartmess
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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 |
| 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. |
| 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. |
| ΔrG° | 384.0 ± 3.0 | kcal/mol | IMRB | DePuy, Kass, et al., 1988 | gas phase; Comparable to water in acidity |
| ΔrG° | <376.3 ± 2.0 | kcal/mol | IMRB | Bruins, Ferrer-Correia, et al., 1978 | gas phase; O- deprotonates |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Schafman and Wenthold, 2007
Schafman, B.S.; Wenthold, P.G.,
Regioselectivity of pyridine deprotonation in the gas phase,
J. Org. Chem., 2007, 72, 5, 1645-1651, https://doi.org/10.1021/jo062117x
. [all data]
Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A.,
Carbon Acidities of Aromatic Compounds,
J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003
. [all data]
Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B.,
Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine,
J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z
. [all data]
DePuy, Kass, et al., 1988
DePuy, C.H.; Kass, S.R.; Bean, G.P.,
Formation and Reactions of Heteroaromatic Anions in the Gas Phase,
J. Org. Chem., 1988, 53, 19, 4427, https://doi.org/10.1021/jo00254a001
. [all data]
Bruins, Ferrer-Correia, et al., 1978
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]
Notes
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- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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