p-pyridinyl-CH2 anion

Formula: C₆H₆N^-
Molecular weight: 92.1191
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Reaction thermochemistry data

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Individual Reactions

C₆H₆N^- + =

By formula: C₆H₆N^- + H⁺ = C₆H₇N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1547. ± 21.	kJ/mol	G+TS	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.
Δ_rH°	1568. ± 13.	kJ/mol	G+TS	DePuy, Kass, et al., 1988	gas phase; Acid: p-methylpyridine. Between iPrOH, MeCN.
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1518. ± 21.	kJ/mol	IMRB	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.
Δ_rG°	1540. ± 13.	kJ/mol	IMRB	DePuy, Kass, et al., 1988	gas phase; Acid: p-methylpyridine. Between iPrOH, MeCN.

Gas phase ion energetics data

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Data compiled by: John E. Bartmess

Protonation reactions

C₆H₆N^- + =

By formula: C₆H₆N^- + H⁺ = C₆H₇N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1547. ± 21.	kJ/mol	G+TS	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.
Δ_rH°	1568. ± 13.	kJ/mol	G+TS	DePuy, Kass, et al., 1988	gas phase; Acid: p-methylpyridine. Between iPrOH, MeCN.
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1518. ± 21.	kJ/mol	IMRB	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.
Δ_rG°	1540. ± 13.	kJ/mol	IMRB	DePuy, Kass, et al., 1988	gas phase; Acid: p-methylpyridine. Between iPrOH, MeCN.

References

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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]

Notes

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Symbols used in this document:

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions