Azobenzene

• Formula: C₁₂H₁₀N₂
• Molecular weight: 182.2212
• IUPAC Standard InChI: InChI=1S/C12H10N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H Copy

  
• IUPAC Standard InChIKey: DMLAVOWQYNRWNQ-UHFFFAOYSA-N Copy
• 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:
  • Azobenzene, (E)-
• 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
• Information on this page:
  • 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
  • Notes
• Data at other public NIST sites:
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C₁₂H₁₀N₂ =

By formula: C₁₂H₁₀N₂ = C₁₂H₁₀N₂

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:
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

Appearance energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (KBr PELLET); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas; HP-GC/MS/IRD

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

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

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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, 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.

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]

den Hertog, Henkens, et al., 1952
den Hertog, H.J.; Henkens, C.H.; van Roon, J.H., Reactivity of 4-nitropyridine-n-oxide (III) Reduction in alkaline medium, Recl. Trav. Chim. Pays-Bas, 1952, 71, 1145-1151. [all data]

Delley and Friedrich, 1977
Delley, R.; Friedrich, K., System CG 72 von bevorzugten Trennflüssigkeiten für die Gas-Chromatographie, Chromatographia, 1977, 10, 10, 593-600, https://doi.org/10.1007/BF02265037 . [all data]

Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C., Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses, J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1 . [all data]

Zenkevich, 1994
Zenkevich, I.G., Contemporary State of Informational Maintenance for Gas Chromatographic Identification of Chlorinated Polycyclic Aromatic Compounds, Zh. Ecol. Khim., 1994, 3, 2, 111-119. [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

Notes

Go To: Top, 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:
  

  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
  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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