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1H-Imidazole

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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
RCD - Robert C. Dunbar
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

imidazolide anion + Hydrogen cation = 1H-Imidazole

By formula: C3H3N2- + H+ = C3H4N2

Quantity Value Units Method Reference Comment
Deltar1464.1 ± 3.0kJ/molG+TSGianola, Ichino, et al., 2005gas phase; B
Deltar1465. ± 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
Deltar1433.4 ± 1.7kJ/molIMREGianola, Ichino, et al., 2005gas phase; B
Deltar1434. ± 8.4kJ/molIMRETaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale; B

Sodium ion (1+) + 1H-Imidazole = (Sodium ion (1+) bullet 1H-Imidazole)

By formula: Na+ + C3H4N2 = (Na+ bullet C3H4N2)

Quantity Value Units Method Reference Comment
Deltar140. ± 5.0kJ/molCIDTHuang and Rodgers, 2002RCD
Deltar140. ± 5.4kJ/molCIDTArmentrout and Rodgers, 2000RCD
Deltar140. ± 5.0kJ/molCIDTRodgers and Armentrout, 1999RCD

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

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

Quantity Value Units Method Reference Comment
Deltar110.kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar123.J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

C3H4N2+ + 1H-Imidazole = (C3H4N2+ bullet 1H-Imidazole)

By formula: C3H4N2+ + C3H4N2 = (C3H4N2+ bullet C3H4N2)

Quantity Value Units Method Reference Comment
Deltar99.2kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar90.8J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

C4H12N+ + 1H-Imidazole = (C4H12N+ bullet 1H-Imidazole)

By formula: C4H12N+ + C3H4N2 = (C4H12N+ bullet C3H4N2)

Quantity Value Units Method Reference Comment
Deltar94.6kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar88.7J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

MeCO2 anion + 1H-Imidazole = (MeCO2 anion bullet 1H-Imidazole)

By formula: C2H3O2- + C3H4N2 = (C2H3O2- bullet C3H4N2)

Quantity Value Units Method Reference Comment
Deltar116.kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar102.J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

1H-Imidazole, 1-acetyl- + Water = 1H-Imidazole + Acetic acid

By formula: C5H6N2O + H2O = C3H4N2 + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-20.2 ± 0.2kJ/molCmWadso, 1960liquid phase; solvent: Aqueous; Heat of hydrolysis; ALS

Acetylimidazole diethyl acetal + Water = Ethyl Acetate + 1H-Imidazole + Ethanol

By formula: C9H16N2O2 + H2O = C4H8O2 + C3H4N2 + C2H6O

Quantity Value Units Method Reference Comment
Deltar-44.69 ± 0.67kJ/molCmGuthrie and Pike, 1987liquid phase; Heat of hydrolysis; ALS

1-(Dimethoxy-phenylmethyl)-1H-imidazole + Water = 1H-Imidazole + Methyl Alcohol + Benzoic acid, methyl ester

By formula: C12H14N2O2 + H2O = C3H4N2 + CH4O + C8H8O2

Quantity Value Units Method Reference Comment
Deltar-55.48 ± 0.71kJ/molCmGuthrie and Pike, 1987liquid phase; Heat of hydrolysis; ALS

N-Formylimidazole diethyl acetal + Water = Ethyl formate + 1H-Imidazole + Ethanol

By formula: C8H14N2O2 + H2O = C3H6O2 + C3H4N2 + C2H6O

Quantity Value Units Method Reference Comment
Deltar-34.6 ± 1.8kJ/molCmGuthrie and Pike, 1987liquid phase; Heat of hydrolysis; ALS

1-Butanamine + 1H-Imidazole, 1-acetyl- = Acetamide, N-butyl- + 1H-Imidazole

By formula: C4H11N + C5H6N2O = C6H13NO + C3H4N2

Quantity Value Units Method Reference Comment
Deltar-75.6 ± 0.3kJ/molCmWadso, 1962solid phase; ALS

Lithium ion (1+) + 1H-Imidazole = (Lithium ion (1+) bullet 1H-Imidazole)

By formula: Li+ + C3H4N2 = (Li+ bullet C3H4N2)

Quantity Value Units Method Reference Comment
Deltar211. ± 9.6kJ/molCIDTHuang and Rodgers, 2002RCD

Potassium ion (1+) + 1H-Imidazole = (Potassium ion (1+) bullet 1H-Imidazole)

By formula: K+ + C3H4N2 = (K+ bullet C3H4N2)

Quantity Value Units Method Reference Comment
Deltar109. ± 5.4kJ/molCIDTHuang and Rodgers, 2002RCD

References

Go To: Top, Reaction thermochemistry 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]

Huang and Rodgers, 2002
Huang, H.; Rodgers, M.T., Sigma versus Pi interactions in alkali metal ion binding to azoles: Threshold collision-induced dissociation and ab initio theory studies, J. Phys. Chem. A, 2002, 106, 16, 4277, https://doi.org/10.1021/jp013630b . [all data]

Armentrout and Rodgers, 2000
Armentrout, P.B.; Rodgers, M.T., An Absolute Sodium Cation Affinity Scale: Threshold Collision-Induced Dissociation Experiments and ab Initio Theory, J. Phys. Chem A, 2000, 104, 11, 2238, https://doi.org/10.1021/jp991716n . [all data]

Rodgers and Armentrout, 1999
Rodgers, M.T.; Armentrout, P.B., Absolute Alkali Metal Ion Binding Affinities of Several Azoles Determined by Threshold Collision-Induced Dissociation, Int. J. Mass Spectrom. Ion Proc., 1999, 185/186/187, 359. [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]

Wadso, 1960
Wadso, I., Heats of hydrolysis of N-acetylated imidazole, 1,2,4-triazole and tetrazole, Acta Chem. Scand., 1960, 14, 903-908. [all data]

Guthrie and Pike, 1987
Guthrie, J.P.; Pike, D.C., Hydration of acylimidazoles: tetrahedral intermediates in acylimidazole hydrolysis and nucleophilic attack by imidazole on esters. The question of concerted mechanisms for acyl transfers, Can. J. Chem., 1987, 65, 1951-1969. [all data]

Wadso, 1962
Wadso, I., Heats of aminolysis and hydrolysis of some N-acetyl compounds and of acetic anhydride, Acta Chem. Scand., 1962, 16, 471-478. [all data]


Notes

Go To: Top, Reaction thermochemistry data, References