1,2-Benzenediamine

• Formula: C₆H₈N₂
• Molecular weight: 108.1411
• IUPAC Standard InChI: InChI=1S/C6H8N2/c7-5-3-1-2-4-6(5)8/h1-4H,7-8H2 Copy

  
• IUPAC Standard InChIKey: GEYOCULIXLDCMW-UHFFFAOYSA-N Copy
• CAS Registry Number: 95-54-5
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: o-Phenylenediamine; o-Benzenediamine; o-Diaminobenzene; C.I. Oxidation Base 16; C.I. 76010; Orthamine; 1,2-Diaminobenzene; 1,2-Phenylenediamine; 2-Aminoaniline; o-Aminoaniline; EK 1700; OPDA; PODA; SQ 15500; o-Fenylendiamin; 1,2-Fenylendiamin; NSC 5354; IK 3
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • UV/Visible spectrum
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

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
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of fusion

Entropy of fusion

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₆H₈N₂⁺ (ion structure unspecified)

Ionization energy determinations

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

Gas Phase Spectrum

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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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.

Contineanu, Wagner, et al., 1982
Contineanu, I.; Wagner, L.; Stanescu, L.; Marchidan, D.I., Combustion and formation enthalpies of o-phenylenediamine, urea and 2-benzimidazolone, Rev. Roum. Chim., 1982, 27, 205-209. [all data]

Kunyavskaya, Karyakin, et al., 1973
Kunyavskaya, S.G.; Karyakin, N.V.; Krylova, G.P.; Chernova, V.I.; Rabinovich, I.B., Heat capacity and thermodynamic properties of iosmeric phenylenediamines, Tr. Khim. Khim. Tekhnol., 1973, 58-59. [all data]

Karyakin, Rabinovich, et al., 1978
Karyakin, N.V.; Rabinovich, I.B.; Sokolov, L.B., Thermodynamics of the synthesis of isomeric poly(phenylenephthalamides), Vysokomol. Soedin. Ser. B, 1978, 20, 662-666. [all data]

Bret-Dibat and Lichanot, 1989
Bret-Dibat, P.; Lichanot, A., Thermodynamic properties of positional isomers of disubstituted benzene in condensed phase, Thermochim. Acta, 1989, 147(2), 261-271. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Richards and Mathews, 1908
Richards, T.W.; Mathews, J.H., The Relation Between Compressibility, Surface Tension, and Other Properties of Material, J. Am. Chem. Soc., 1908, 30, 8-13. [all data]

Perkin, 1896
Perkin, W.H., LXIX. On Magnetic Rotatory Power, especially of Aromatic Compounds, J. Chem. Soc., 1896, 69, 1025-1257. [all data]

Bret-Dibat and Lichanot, 1989, 2
Bret-Dibat, P.; Lichanot, A., Proprietes thermodynamiques des isomeres de position de benzenes disubstitues en phase condensee, Thermochim. Acta, 1989, 147, 2, 261, https://doi.org/10.1016/0040-6031(89)85181-0 . [all data]

Kemula, Buchowski, et al., 1968
Kemula, W.; Buchowski, H.; Pawlowski, W., Effect of the position of substituents in an aromatic ring on R(f) and partition coefficients: II. aromatic amines, Rocz. Chem., 1968, 42, 1951. [all data]

Sabbah and Perez, 1997
Sabbah, Raphaël; Perez, Laurence, Energétique des liaisons inter- et intramoléculaires dans les trois isomères du benzènediamine, Can. J. Chem., 1997, 75, 4, 357-364, https://doi.org/10.1139/v97-041 . [all data]

Lee, Chang, et al., 1997
Lee, Ming-Jer; Chang, Yao-Kun; Lin, Ho-mu; Chen, Chang-Hsin, Solid-Liquid Equilibria for 4-Methoxyphenol with Catechol, Ethylenediamine, or Piperazine, J. Chem. Eng. Data, 1997, 42, 2, 349-352, https://doi.org/10.1021/je960201b . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Tsuji, Saito, et al., 1973
Tsuji, K.; Saito, M.; Tani, T., Ionization potentials of phenylenediamines and steric effect in the ortho isomer, Denki Kagaku oyobi Kogyo Butsuri Kagaku, 1973, 41, 688. [all data]

Farrell and Newton, 1966
Farrell, P.G.; Newton, J., Ionization potentials of primary aromatic amines and aza-hydrocarbons, Tetrahedron Lett., 1966, 5517. [all data]

Kinoshita, 1962
Kinoshita, M., The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil, Bull. Chem. Soc. Japan, 1962, 35, 1609. [all data]

Crable and Kearns, 1962
Crable, G.F.; Kearns, G.L., Effect of substituent groups on the ionization potentials of benzenes, J. Phys. Chem., 1962, 66, 436. [all data]

Briegleb and Czekalla, 1959
Briegleb, G.; Czekalla, J., Die Bestimmung von lonisierungsenergien aus den Spektren von Elektronenubergangskomplexen, Z.Elektrochem., 1959, 63, 6. [all data]

Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Spiers, M.; Ridyard, J.N.A., The electronic structure of substituted benzenes; a study of aniline, the toluidines, phenylenediamines and fluoroanilines by photoelectron spectroscopy and ab initio calculations, J. Mol. Struct., 1979, 53, 235. [all data]

Streets, Hall, et al., 1972
Streets, D.G.; Hall, W.E.; Ceasar, G.P., Mesomeric mixing in the π energy levels of aminobenzenes studied by photoelectron spectroscopy, Chem. Phys. Lett., 1972, 17, 90. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  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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