1H-Benzotriazole
- Formula: C6H5N3
- Molecular weight: 119.1240
- IUPAC Standard InChI: InChI=1S/C6H5N3/c1-2-4-6-5(3-1)7-9-8-6/h1-4H,(H,7,8,9)
- IUPAC Standard InChIKey: QRUDEWIWKLJBPS-UHFFFAOYSA-N
- CAS Registry Number: 95-14-7
- 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: Azimidobenzene; Aziminobenzene; Benzene azimide; Benzisotriazole; Benzotriazole; Benztriazole; Cobratec 99; 1,2-Aminoazophenylene; 1,2,3-Benzotriazole; 1,2,3-Triaza-1H-indene; 1,2,3-Triazaindene; 1H-1,2,3-Benzotriazole; 2,3-Diazaindole; Cobratec No. 99; NCI-C03521; NSC-3058; U-6233; 1,2,3-Benztriazole; Cobratec 35G; 1,2,3-1H-Benzotriazole
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Gas phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 335.5 ± 1.3 | kJ/mol | Ccb | Jimenez, Roux, et al., 1989 |
Condensed phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 236.5 ± 1.2 | kJ/mol | Ccb | Jimenez, Roux, et al., 1989 | ALS |
| ΔfH°solid | 250.0 ± 1.1 | kJ/mol | Ccb | Fagley, Klein, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = 249.6 kJ/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3312.2 ± 0.8 | kJ/mol | Ccb | Jimenez, Roux, et al., 1989 | ALS |
| ΔcH°solid | -3315. | kJ/mol | Ccb | Zimmerman and Geisenfelder, 1961 | ALS |
| ΔcH°solid | -3325.6 ± 1.0 | kJ/mol | Ccb | Fagley, Klein, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = -3326.2 ± 0.88 kJ/mol; ALS |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 178.7 | 298.15 | Jimenez, Roux, et al., 1989 | DH |
Phase change 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:
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔsubH° | 98.2 ± 0.7 | kJ/mol | C | Sabbah and Perez, 1999 | AC |
| ΔsubH° | 99.0 ± 0.5 | kJ/mol | V | Jimenez, Roux, et al., 1989 | ALS |
| ΔsubH° | 99.0 ± 0.5 | kJ/mol | ME | Jimenez, Roux, et al., 1989 | AC |
| ΔsubH° | 97.9 | kJ/mol | V | Zimmerman and Geisenfelder, 1961 | ALS |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 7.7 | 369.9 | Sabbah and Perez, 1999 | AC |
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 as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.20 ± 0.05 | EI | Thorstad and Undheim, 1974 | LLK |
De-protonation reactions
C6H4N3- + =
By formula: C6H4N3- + H+ = C6H5N3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1415. ± 8.8 | kJ/mol | G+TS | Catalan, Claramunt, et al., 1988 | gas phase; Revised: 91TAF; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1384. ± 8.4 | kJ/mol | IMRE | Catalan, Claramunt, et al., 1988 | gas phase; Revised: 91TAF; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
Jimenez, Roux, et al., 1989
Jimenez, P.; Roux, M.V.; Turrion, C.,
Thermochemical properties of N-heterocyclic compounds II. Enthalpies of combustion, vapour pressures, enthalpies of sublimation, and enthalpies of formation of 1,2,4-triazole and benzotriazole,
J. Chem. Thermodyn., 1989, 21, 759-764. [all data]
Fagley, Klein, et al., 1953
Fagley, T.F.; Klein, E.; Albrecht, J.F., Jr.,
The heats of combustion of diazoaminobenzene, benzotriazole and 2-triazoethanol,
J. Am. Chem. Soc., 1953, 75, 3104-31. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Zimmerman and Geisenfelder, 1961
Zimmerman, H.; Geisenfelder, H.,
Uber die Mesomerieenergie von Azolen,
Z. Electrochem., 1961, 65, 368-371. [all data]
Sabbah and Perez, 1999
Sabbah, Raphaël; Perez, Laurence,
Energetics of Intramolecular Bonds in 1H-1,2,4-Triazole and 1H-Benzotriazole,
Aust. J. Chem., 1999, 52, 4, 235-621, https://doi.org/10.1071/C99006
. [all data]
Thorstad and Undheim, 1974
Thorstad, O.; Undheim, K.,
Mass spectrometry of onium compounds. XXIV. Ionisation potential in structure analysis of pyridodiazo-oxides,
Chem. Scr., 1974, 6, 222. [all data]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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