imidazolide anion
- Formula: C3H3N2-
- Molecular weight: 67.0699
- IUPAC Standard InChI: InChI=1S/C3H3N2/c1-2-5-3-4-1/h1-3H/q-1
- IUPAC Standard InChIKey: JBFYUZGYRGXSFL-UHFFFAOYSA-N
- CAS Registry Number: 36954-03-7
- Chemical structure:
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Reaction thermochemistry data
Go To: Top, References, Notes
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
+
=
By formula: C3H3N2- + H+ = C3H4N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 349.93 ± 0.72 | kcal/mol | G+TS | Gianola, Ichino, et al., 2005 | gas phase; B |
| ΔrH° | 350.1 ± 2.1 | kcal/mol | G+TS | Taft, Anvia, et al., 1986 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 342.60 ± 0.40 | kcal/mol | IMRE | Gianola, Ichino, et al., 2005 | gas phase; B |
| ΔrG° | 342.8 ± 2.0 | kcal/mol | IMRE | Taft, Anvia, et al., 1986 | gas phase; value altered from reference due to change in acidity scale; B |
( • 2
) +
= (
• 3
)
By formula: (C3H3N2- • 2H2O) + H2O = (C3H3N2- • 3H2O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 12.9 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 29.2 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
( •
) +
= (
• 2
)
By formula: (C3H3N2- • H2O) + H2O = (C3H3N2- • 2H2O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 11.8 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 18.2 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
+
= (
•
)
By formula: C3H3N2- + C6H11NO3 = (C3H3N2- • C6H11NO3)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 23.1 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 24.8 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
+
= (
•
)
By formula: C3H3N2- + H2O = (C3H3N2- • H2O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.2 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 22.6 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
+
= (
•
)
By formula: C3H3N2- + C3H4N2 = (C3H3N2- • C3H4N2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 26.4 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 29.3 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
+
= (
•
)
By formula: C3H3N2- + CH4O = (C3H3N2- • CH4O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 17.1 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 24.2 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
+
= (
•
)
By formula: C3H3N2- + CHN = (C3H3N2- • CHN)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 23.9 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 21.9 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
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]
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, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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