1H-Benzotriazole
- Formula: C6H5N3
- Molecular weight: 119.1240
- 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 |
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° | 1415. ± 8.8 | kJ/mol | G+TS | Catalan, Claramunt, et al., 1988 | gas phase; Revised: 91TAF |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1384. ± 8.4 | kJ/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° | 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 |
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 |
UV/Visible spectrum
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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Source | Ramart-Lucas, Hoch, et al., 1949 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 112 |
Instrument | n.i.g. |
Melting point | 100 |
Boiling point | 204(15) |
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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]
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]
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]
Ramart-Lucas, Hoch, et al., 1949
Ramart-Lucas, M.; Hoch, J.; Grumez, M.,
Deformation des orbites electroniques de l'azote par cyclisation (serie du benzotriazole et du phenyltriazole),
Bull. Soc. Chim. Fr., 1949, 16, 447-454. [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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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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