Azobenzene
- Formula: C12H10N2
- Molecular weight: 182.2212
- IUPAC Standard InChIKey: DMLAVOWQYNRWNQ-UHFFFAOYSA-N
- CAS Registry Number: 103-33-3
- 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. - Species with the same structure:
- Other names: Diazene, diphenyl-; Azobenzide; Azobenzol; Benzene, azobis-; Benzene, azodi-; Benzeneazobenzene; Diazobenzene; Diphenyldiimide; 1,2-Diphenyldiazene; Azobenzeen; Azobisbenzene; Azodibenzeneazofume; Azofume; Benzofume; Diphenyldiazene; ENT 14,611; NCI-C02926; USAF EK-704; Azodibenzene; Azobenzen; Diazene, 1,2-diphenyl-; NSC 2102
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 374. | kJ/mol | Ccb | Lemoult, 1908 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -6452. | kJ/mol | Ccb | Wieland, Heymann, et al., 1934 | |
ΔcH°solid | -6468.1 ± 3.8 | kJ/mol | Ccb | Swietoslawski and Bobinska, 1929 | |
ΔcH°solid | -6525.8 | kJ/mol | Ccb | Lemoult, 1908 |
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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
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 |
---|---|---|---|---|---|
Tboil | 566.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 341. | K | N/A | Bergmann, Fischer, et al., 1953 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 340. | K | N/A | Sorum and Durand, 1952 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 93.84 ± 0.12 | kJ/mol | V | Cammenga, Behrens, et al., 1977 | Hfusion=22.7 kJ/mol; ALS |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
376.7 to 566. | 5.09177 | 2671.499 | -41.23 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
22.368 | 340.5 | Cingolani and Berchiesi, 1974 | DH |
22.389 | 342.2 | Eykman, 1889 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
65.59 | 340.5 | Cingolani and Berchiesi, 1974 | DH |
65.4 | 342.2 | Eykman, 1889 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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 as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.5 ± 0.05 | EI | Natalis and Franklin, 1981 | LLK |
8.4 | PE | Petrachenko, Vovna, et al., 1993 | Vertical value; LL |
8.4 | PE | Furin, Petrachenko, et al., 1989 | Vertical value; LL |
8.5 | PE | Rao, 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H5+ | 11.9 ± 0.1 | C6H5+N2 | EI | Natalis and Franklin, 1981 | LLK |
C6H5N2+ | 9.8 ± 0.1 | C6H5 | EI | Natalis and Franklin, 1981 | LLK |
C12H8+ | 14.7 ± 0.05 | N2+2H | EI | Natalis and Franklin, 1981 | LLK |
C12H9+ | 12.4 ± 0.1 | N2+H | EI | Natalis and Franklin, 1981 | LLK |
C12H10+ | 11.6 ± 0.2 | N2 | EI | Natalis and Franklin, 1981 | LLK |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 113361 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Lemoult, 1908
Lemoult, M.P.,
Recherches theoriques et experimentales sur les chaleurs de combustion et de formation des composes organiques,
Ann. Chim. Phys., 1908, 14, 289-310. [all data]
Wieland, Heymann, et al., 1934
Wieland, H.; Heymann, K.; Tsatsas, T.; Juchum, D.; Varvoglis, G.; Labriola, G.; Dobbelstein, O.; Boyd-Barrett, H.S.,
Uber das Auftreten freier Radikale bei chemischen Reaktionen. VIII,
Ann., 1934, 514, 145-181. [all data]
Swietoslawski and Bobinska, 1929
Swietoslawski, M.W.; Bobinska, M.J.,
O cieple spalania kamfory, azobenzenu i hydrazobenzenu - Sur la chaleur de combustion du comphre, de l'hydrazobenzene,
Rocz. Chem., 1929, 9, 723-730. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Bergmann, Fischer, et al., 1953
Bergmann, E.D.; Fischer, E.; Jaffe, J.H.,
Exalted Distortion Polarizations of Some COlored Hydrocarbons,
J. Am. Chem. Soc., 1953, 75, 3230-3. [all data]
Sorum and Durand, 1952
Sorum, C.H.; Durand, E.A.,
The Melting of Binary Eutectics,
J. Am. Chem. Soc., 1952, 74, 1071. [all data]
Cammenga, Behrens, et al., 1977
Cammenga, H.K.; Behrens, E.; Wolf, F.,
Thermal isomerization of cis-azobenzene in the solid state
in React. Solids, [Proc. Int. Symp.],, ed. J. Wood, O. Lindqvist, C. Helgesson, Plenum: New York,NY, 1977, 481-486. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Cingolani and Berchiesi, 1974
Cingolani, A.; Berchiesi, G.,
Thermodynamic properties of organic compounds. 1. A DSC study of phase transitions in aliphatic dicarboxylic acids,
J. Therm. Anal., 1974, 6, 87-90. [all data]
Eykman, 1889
Eykman, J.F.,
Zur kryoskopischen Molekulargewichtsbestimmung,
Z. Physik. Chem., 1889, 4, 497-519. [all data]
Natalis and Franklin, 1981
Natalis, P.; Franklin, J.L.,
Ionization and dissociation of diphenyl and condensed-ring aromatics by electron impact. III. Azobenzene,
Int. J. Mass Spectrom. Ion Phys., 1981, 40, 35. [all data]
Petrachenko, Vovna, et al., 1993
Petrachenko, N.E.; Vovna, V.I.; Furin, G.G.,
Photoelectron HeI spectra of fluorinated azo- and azoxy-benzenes,
J. Fluorine Chem., 1993, 63, 85. [all data]
Furin, Petrachenko, et al., 1989
Furin, G.G.; Petrachenko, N.E.; Vovna, V.I.,
Photoelectron spectra of fluorine-containing azoxybenzenes,
J. Org. Chem. USSR, 1989, 26, 1725, In original 1998. [all data]
Rao, 1975
Rao, C.N.R.,
Lone-pair ionization bands of chromophores in the photoelectron spectra of organic molecules,
Indian J. Chem., 1975, 13, 950. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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