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Pyrazine

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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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar

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Individual Reactions

C4H3N2- + Hydrogen cation = Pyrazine

By formula: C4H3N2- + H+ = C4H4N2

Quantity Value Units Method Reference Comment
Deltar392.6 ± 2.5kcal/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.; B
Quantity Value Units Method Reference Comment
Deltar383.50 ± 0.40kcal/molN/AWren, Vogelhuber, et al., 2012gas phase; B
Deltar383.1 ± 2.0kcal/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.; B

3Hydrogen + Pyrazine = Piperazine

By formula: 3H2 + C4H4N2 = C4H10N2

Quantity Value Units Method Reference Comment
Deltar49.52 ± 0.67kcal/molChydHafelinger and Steinmann, 1977liquid phase; solvent: Acetic acid; ALS

Lithium ion (1+) + Pyrazine = (Lithium ion (1+) bullet Pyrazine)

By formula: Li+ + C4H4N2 = (Li+ bullet C4H4N2)

Quantity Value Units Method Reference Comment
Deltar35.6 ± 3.3kcal/molCIDTAmunugama and Rodgers, 2000RCD

Sodium ion (1+) + Pyrazine = (Sodium ion (1+) bullet Pyrazine)

By formula: Na+ + C4H4N2 = (Na+ bullet C4H4N2)

Quantity Value Units Method Reference Comment
Deltar25.7 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2000RCD

Potassium ion (1+) + Pyrazine = (Potassium ion (1+) bullet Pyrazine)

By formula: K+ + C4H4N2 = (K+ bullet C4H4N2)

Quantity Value Units Method Reference Comment
Deltar16.1 ± 0.9kcal/molCIDTAmunugama and Rodgers, 2000RCD

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.

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]

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]

Hafelinger and Steinmann, 1977
Hafelinger, G.; Steinmann, L., Heat of hydrogenation of compounds containing isolated and conjugted C=N bouble bonds, Angew. Chem. Int. Ed. Engl., 1977, 16, 47-48. [all data]

Amunugama and Rodgers, 2000
Amunugama, R.; Rodgers, M.T., Absolute Alkali Metal Ion Binding Affinities of Several Azines Determined by Threshold Collision-Induced Dissociation and Ab Initio Theory, Int. J. Mass Spectrom., 2000, 195/196, 439, https://doi.org/10.1016/S1387-3806(99)00145-1 . [all data]


Notes

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