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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

imidazolide anion + Hydrogen cation = 1H-Imidazole

By formula: C3H3N2- + H+ = C3H4N2

Quantity Value Units Method Reference Comment
Δr349.93 ± 0.72kcal/molG+TSGianola, Ichino, et al., 2005gas phase; B
Δr350.1 ± 2.1kcal/molG+TSTaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr342.60 ± 0.40kcal/molIMREGianola, Ichino, et al., 2005gas phase; B
Δr342.8 ± 2.0kcal/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
Δr12.9kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr29.2cal/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
Δr11.8kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr18.2cal/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
Δr23.1kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr24.8cal/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
Δr15.2kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr22.6cal/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
Δr26.4kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr29.3cal/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
Δr17.1kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr24.2cal/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
Δr23.9kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr21.9cal/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
Δr349.93 ± 0.72kcal/molG+TSGianola, Ichino, et al., 2005gas phase
Δr350.1 ± 2.1kcal/molG+TSTaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr342.60 ± 0.40kcal/molIMREGianola, Ichino, et al., 2005gas phase
Δr342.8 ± 2.0kcal/molIMRETaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale

Ion clustering 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

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

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

Quantity Value Units Method Reference Comment
Δr23.9kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase
Quantity Value Units Method Reference Comment
Δr21.9cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase

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

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

Quantity Value Units Method Reference Comment
Δr17.1kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase
Quantity Value Units Method Reference Comment
Δr24.2cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase

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

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

Quantity Value Units Method Reference Comment
Δr26.4kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase
Quantity Value Units Method Reference Comment
Δr29.3cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase

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
Δr23.1kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase
Quantity Value Units Method Reference Comment
Δr24.8cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase

imidazolide anion + Water = (imidazolide anion • Water)

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

Quantity Value Units Method Reference Comment
Δr15.2kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase
Quantity Value Units Method Reference Comment
Δr22.6cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase

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

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

Quantity Value Units Method Reference Comment
Δr11.8kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase
Quantity Value Units Method Reference Comment
Δr18.2cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase

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

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

Quantity Value Units Method Reference Comment
Δr12.9kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase
Quantity Value Units Method Reference Comment
Δr29.2cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase

References

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

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References