1H-1,2,3-Triazole
- Formula: C2H3N3
- Molecular weight: 69.0653
- IUPAC Standard InChI: InChI=1S/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5)
- IUPAC Standard InChIKey: QWENRTYMTSOGBR-UHFFFAOYSA-N
- CAS Registry Number: 288-36-8
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: V-triazole; Osotriazole; Pyrrodiazole; Triazacyclopentadiene; 1,2,3-Triazole
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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
RCD - Robert C. Dunbar
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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Individual Reactions
C2H2N3- + =
By formula: C2H2N3- + H+ = C2H3N3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1449. ± 8.8 | kJ/mol | G+TS | Catalan, Claramunt, et al., 1988 | gas phase; The authors state the acidity is for the 2H isomer, which is more stable(G3MP2B3)in the gas phase than the 1H isomer by 3 kcal/mol. However, only the 1H isomer is commercially available; thus, this may not be a clean equilibrium.; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1419. ± 8.4 | kJ/mol | IMRE | Catalan, Claramunt, et al., 1988 | gas phase; The authors state the acidity is for the 2H isomer, which is more stable(G3MP2B3)in the gas phase than the 1H isomer by 3 kcal/mol. However, only the 1H isomer is commercially available; thus, this may not be a clean equilibrium.; B |
+
= (
•
)
By formula: Na+ + C2H3N3 = (Na+ • C2H3N3)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 95.8 ± 4.6 | kJ/mol | CIDT | Rodgers and Armentrout, 1999 | RCD |
Free energy of reaction
| ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 0.0 | 0. | CIDT | Rodgers and Armentrout, 1999 | RCD |
=
By formula: C2H3N3 = C2H3N3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 12. | kJ/mol | Eqk | Mauret, Fayet, et al., 1973 | liquid phase; solvent: Benzene; ALS |
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.
Catalan, Claramunt, et al., 1988
Catalan, J.; Claramunt, R.M.; Elguero, J.; Menedez, M.; Anvia, F.; Quian, J.H.; Taagepera, M.; Taft, R.W.,
Basicity and Acidity of Azoles. The Annelation Effect in Azoles.,
J. Am. Chem. Soc., 1988, 110, 13, 4107, https://doi.org/10.1021/ja00221a001
. [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]
Mauret, Fayet, et al., 1973
Mauret, P.; Fayet, J.P.; Fabre, M.; Elguero, J.; Pardo, M.d.C.,
Tautomerism study of υ-triazole from dipolar moment measurements,
J. Chim. Phys. Phys.-Chim. Biol., 1973, 70, 1483-1485. [all data]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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