1,3-Phenylenediamine

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

  
• IUPAC Standard InChIKey: WZCQRUWWHSTZEM-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-45-2
• 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: 1,3-Benzenediamine; m-Phenylenediamine; m-Aminoaniline; m-Benzenediamine; m-Diaminobenzene; C.I. Developer 11; Developer C; Developer H; Developer M; Direct Brown BR; Direct Brown GG; 1,3-Diaminobenzene; 3-Aminoaniline; m-Fenylendiamin; C.I. 76025; Developer 11; Metaphenylenediamine; Phenylenediamine, m; APCO 2330; Phenylenediamine, meta; NSC 4776; UN-1673
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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)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• 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 as indicated in comments:
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Constant pressure heat capacity of liquid

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
DH - Eugene S. Domalski and Elizabeth D. Hearing
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Antoine Equation Parameters

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

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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)

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, 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

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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, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

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), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

Rabinovich, Karyakin, et al., 1984
Rabinovich, I.B.; Karyakin, N.V.; Dzharimova, E.S.; Siling, S.A.; Ponomarev, I.I.; Vinogradova, S.V., Thermodynamics of condensation of phthalonitrile with m-phenylenediamine, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1984, 716-723. [all data]

Rabinovich, Karyakin, et al., 1984, 2
Rabinovich, I.B.; Karyakin, N.V.; Dzharimova, E.S.; Siling, S.A.; Ponomarev, I.I.; Vinogradova, S.V., Thermodynamics of the condensation of o-phthalic acid dinitrile with m-phenylenediamine, Izv. Akad. Nauk SSSR, Ser. Khim., 1984, (4), 779-787. [all data]

Lesbats and Lichanot, 1987
Lesbats, C.; Lichanot, A., Capacites calorifiques de durcisseurs amines et resines epoxydes, Thermochim. Acta, 1987, 109, 317-329. [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]

Bret-Dibat and Lichanot, 1989
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]

Rabinovich, Nistratov, et al., 1984
Rabinovich, I.B.; Nistratov, V.P.; Babinkov, A.G.; Siling, S.A.; Ponomarev, I.I.; Vinogradova, S.V., Thermodynamics of the condensation of o-phthalic acid dinitrile with m-phenylenediamine, Izv. Akad. Nauk SSSR, 1984, 1984, 779. [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]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [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]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

Pykhtina, Cherednichenko, et al., 1974
Pykhtina, E.V.; Cherednichenko, L.V.; Kardash, I.E.; Evlasheva, T.I.; Sorokin, V.V.; Potapov, V.K.; Pravednikov, A.N., Ionization potentials of amines and energies of charge transfer bands in the absorption spectra of complexes of 7,7,8,8-tetracyanoquinodimethan, High Energy Chem., 1974, 8, 257, In original 307. [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]

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]

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]

Eggers and Schiebe, 1966
Eggers, J.; Schiebe, G., UV atlas of organic compounds, 1966, 2, D6/1. [all data]

Notes

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

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  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
  Ttriple	Triple point temperature
  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
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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