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p-pyridinide anion


Gas phase ion energetics 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

Electron affinity of neutral species

EAneutral (eV) Method Reference Comment
1.480 ± 0.020N/ACulberson, Blackstone, et al., 2013 
1.4800 ± 0.0060LPESWren, Vogelhuber, et al., 2012 
1.59 ± 0.19D-EASchafman and Wenthold, 2007 
1.54 ± 0.20D-EAMeot-ner and Kafafi, 1988anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
2.411 ± 0.030SIFailes, Joyce, et al., 1976The Magnetron method, lacking mass analysis, is not considered reliable.

Protonation reactions

C5H4N- + Hydrogen cation = Pyridine

By formula: C5H4N- + H+ = C5H5N

Quantity Value Units Method Reference Comment
Deltar1631. ± 8.4kJ/molIMRESchafman and Wenthold, 2007gas phase
Deltar1636. ± 10.kJ/molTDEqMeot-ner and Kafafi, 1988gas 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
Deltar1601. ± 8.4kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
Deltar1607. ± 13.kJ/molIMRBDePuy, Kass, et al., 1988gas phase; Comparable to water in acidity
Deltar<1574. ± 8.4kJ/molIMRBBruins, Ferrer-Correia, et al., 1978gas phase; O- deprotonates

References

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

Culberson, Blackstone, et al., 2013
Culberson, L.M.; Blackstone, C.C.; Sanov, A., Photoelectron Angular Distributions of Pyridinide: A Benchmark Application of the Mixed s-p Model to a Truly Polyatomic Anion, J. Phys. Chem. A, 2013, 117, 46, 11760-11765, https://doi.org/10.1021/jp402507v . [all data]

Wren, Vogelhuber, et al., 2012
Wren, S.W.; Vogelhuber, K.M.; Garver, J.M.; Kato, S.; Sheps, L.; Bierbaum, V.M.; Lineberger, W.C., C-H Bond Strengths and Acidities in Aromatic Systems: Effects of Nitrogen Incorporation in Mono-, Di-, and Triazines, J. Am. Chem. Soc., 2012, 134, 15, 6584-6595, https://doi.org/10.1021/ja209566q . [all data]

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]

Failes, Joyce, et al., 1976
Failes, R.L.; Joyce, J.T.; Walton, E.C., The behaviour of some dimethyl and trimethyl substituted pyridines in the magnetron, J. Phys. D: Appl. Phys., 1976, 9, 1543. [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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