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 | 80.19 ± 0.31 | kcal/mol | Ccb | Jimenez, Roux, et al., 1989 |
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° | 23.5 ± 0.2 | kcal/mol | C | Sabbah and Perez, 1999 | AC |
| ΔsubH° | 23.7 ± 0.1 | kcal/mol | V | Jimenez, Roux, et al., 1989 | ALS |
| ΔsubH° | 23.7 ± 0.1 | kcal/mol | ME | Jimenez, Roux, et al., 1989 | AC |
| ΔsubH° | 23.4 | kcal/mol | V | Zimmerman and Geisenfelder, 1961 | ALS |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 1.8 | 369.9 | Sabbah and Perez, 1999 | AC |
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 by: John E. Bartmess
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
C6H4N3- + =
By formula: C6H4N3- + H+ = C6H5N3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 338.1 ± 2.1 | kcal/mol | G+TS | Catalan, Claramunt, et al., 1988 | gas phase; Revised: 91TAF |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 330.8 ± 2.0 | kcal/mol | IMRE | Catalan, Claramunt, et al., 1988 | gas phase; Revised: 91TAF |
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° | 338.1 ± 2.1 | kcal/mol | G+TS | Catalan, Claramunt, et al., 1988 | gas phase; Revised: 91TAF; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 330.8 ± 2.0 | kcal/mol | IMRE | Catalan, Claramunt, et al., 1988 | gas phase; Revised: 91TAF; B |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | ALPHA Chemicals / NIST MS Data Center. |
| NIST MS number | 125350 |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 1469. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | TC-FFAP | 2629. | Kurose and Yatagai, 2005 | 60. m/0.25 mm/0.4 μm, He, 3. K/min, 220. C @ 30. min; Tstart: 60. C |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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]
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]
Zimmerman and Geisenfelder, 1961
Zimmerman, H.; Geisenfelder, H.,
Uber die Mesomerieenergie von Azolen,
Z. Electrochem., 1961, 65, 368-371. [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]
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]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Kurose and Yatagai, 2005
Kurose, K.; Yatagai, M.,
Components of the essential oils of Azadirachta indica A. Juss, Azadirachta siamensis Velton, and Azadirachta excelsa (Jack) Jacobs and their comparison,
J. Wood Sci., 2005, 51, 2, 185-188, https://doi.org/10.1007/s10086-004-0640-4
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas 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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