imidazolide 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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Individual Reactions

imidazolide anion + Hydrogen cation = 1H-Imidazole

By formula: C3H3N2- + H+ = C3H4N2

Quantity Value Units Method Reference Comment
Δr1464.1 ± 3.0kJ/molG+TSGianola, Ichino, et al., 2005gas phase; B
Δr1465. ± 8.8kJ/molG+TSTaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1433.4 ± 1.7kJ/molIMREGianola, Ichino, et al., 2005gas phase; B
Δr1434. ± 8.4kJ/molIMRETaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale; B

(imidazolide anion • 2Water) + Water = (imidazolide anion • 3Water)

By formula: (C3H3N2- • 2H2O) + H2O = (C3H3N2- • 3H2O)

Quantity Value Units Method Reference Comment
Δr54.0kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr122.J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

(imidazolide anion • Water) + Water = (imidazolide anion • 2Water)

By formula: (C3H3N2- • H2O) + H2O = (C3H3N2- • 2H2O)

Quantity Value Units Method Reference Comment
Δr49.4kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr76.1J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

imidazolide anion + L-Alanine, N-acetyl-, methyl ester = (imidazolide anion • L-Alanine, N-acetyl-, methyl ester)

By formula: C3H3N2- + C6H11NO3 = (C3H3N2- • C6H11NO3)

Quantity Value Units Method Reference Comment
Δr96.7kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr104.J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

imidazolide anion + Water = (imidazolide anion • Water)

By formula: C3H3N2- + H2O = (C3H3N2- • H2O)

Quantity Value Units Method Reference Comment
Δr63.6kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr94.6J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

imidazolide anion + 1H-Imidazole = (imidazolide anion • 1H-Imidazole)

By formula: C3H3N2- + C3H4N2 = (C3H3N2- • C3H4N2)

Quantity Value Units Method Reference Comment
Δr110.kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr123.J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

imidazolide anion + Methyl Alcohol = (imidazolide anion • Methyl Alcohol)

By formula: C3H3N2- + CH4O = (C3H3N2- • CH4O)

Quantity Value Units Method Reference Comment
Δr71.5kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr101.J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

imidazolide anion + Hydrogen cyanide = (imidazolide anion • Hydrogen cyanide)

By formula: C3H3N2- + CHN = (C3H3N2- • CHN)

Quantity Value Units Method Reference Comment
Δr100.kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr91.6J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

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
2.6130 ± 0.0060LPESGianola, Ichino, et al., 2005 

Protonation reactions

imidazolide anion + Hydrogen cation = 1H-Imidazole

By formula: C3H3N2- + H+ = C3H4N2

Quantity Value Units Method Reference Comment
Δr1464.1 ± 3.0kJ/molG+TSGianola, Ichino, et al., 2005gas phase
Δr1465. ± 8.8kJ/molG+TSTaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1433.4 ± 1.7kJ/molIMREGianola, Ichino, et al., 2005gas phase
Δr1434. ± 8.4kJ/molIMRETaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale

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.

Gianola, Ichino, et al., 2005
Gianola, A.J.; Ichino, T.; Hoenigman, R.L.; Kato, S.; Bierbaum, V.M.; Lineberger, W.C., Photoelectron spectra and ion chemistry of imidazolide, J. Phys. Chem. A, 2005, 109, 50, 11504-11514, https://doi.org/10.1021/jp053566o . [all data]

Taft, Anvia, et al., 1986
Taft, R.W.; Anvia, F.; Taagepera, M.; Catalan, J.; Elgueroy, J., Electrostatic proximity effects in the relative basicities of pyrazole, imidazole, pyridazine, and pyrimidine, J. Am. Chem. Soc., 1986, 108, 3237. [all data]

Meot-Ner (Mautner), 1988
Meot-Ner (Mautner), M., Models for Strong Interactions in Proteins and Enzymes. 2. Interactions of Ions with the Peptide Link and Imidazole, J. Am. Chem. Soc., 1988, 110, 10, 3075, https://doi.org/10.1021/ja00218a014 . [all data]


Notes

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