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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
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 |
Condensed phase thermochemistry data
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, 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:
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 | 56.52 ± 0.29 | kcal/mol | Ccb | Jimenez, Roux, et al., 1989 | ALS |
| ΔfH°solid | 59.75 ± 0.26 | kcal/mol | Ccb | Fagley, Klein, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = 59.66 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -791.6 ± 0.2 | kcal/mol | Ccb | Jimenez, Roux, et al., 1989 | ALS |
| ΔcH°solid | -792.2 | kcal/mol | Ccb | Zimmerman and Geisenfelder, 1961 | ALS |
| ΔcH°solid | -794.84 ± 0.25 | kcal/mol | Ccb | Fagley, Klein, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = -794.97 ± 0.21 kcal/mol; ALS |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 42.71 | 298.15 | Jimenez, Roux, et al., 1989 | DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References, Notes
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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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
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), References, Notes
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), 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]
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), 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.