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p-pyridinide anion


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- + 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

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, 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: 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

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics 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]

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]

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]


Notes

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