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1,3-Phenylenediamine

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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

Quantity Value Units Method Reference Comment
Deltafsolid-7.9kJ/molCcbKunyavskaya, Karyakin, et al., 1973see Karyakin, Rabinovich, et al., 1978 and Rabinovich, Karyakin, et al., 1984; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-3497. ± 5.4kJ/molCcbKunyavskaya, Karyakin, et al., 1973see Karyakin, Rabinovich, et al., 1978 and Rabinovich, Karyakin, et al., 1984; ALS
Quantity Value Units Method Reference Comment
solid,1 bar154.5J/mol*KN/ARabinovich, Karyakin, et al., 1984, 2DH
solid,1 bar149.49J/mol*KN/AKunyavskaya, Karyakin, et al., 1973DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
153.7298.Lesbats and Lichanot, 1987T = 220 to 400 K.; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
159.6298.15Rabinovich, Karyakin, et al., 1984, 2T = 13 to 500 K.; DH
161.08300.Kunyavskaya, Karyakin, et al., 1973T = 20 to 300 K.; DH

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

Quantity Value Units Method Reference Comment
Tboil556.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus337.KN/ALesbats and Lichanot, 1987DH
Tfus335.KN/ABret-Dibat and Lichanot, 1989Crystal phase 1 phase; Uncertainty assigned by TRC = 0.4 K; TRC
Quantity Value Units Method Reference Comment
Ttriple339.1KN/ARabinovich, Nistratov, et al., 1984Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Deltasub90.4 ± 0.4kJ/molCSabbah and Perez, 1997AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
63.7387.AStephenson and Malanowski, 1987Based on data from 372. - 559. K. See also Stull, 1947.; AC

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
373.0 - 558.75.117342635.233-43.185Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
15.570339.1Rabinovich, Karyakin, et al., 1984, 2DH
15.4335.5Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
45.92339.1Rabinovich, Karyakin, et al., 1984, 2DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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)

Quantity Value Units Method Reference Comment
Proton affinity (review)929.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity899.2kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
7.14PIPykhtina, Cherednichenko, et al., 1974LLK
7.44PETsuji, Saito, et al., 1973LLK
7.5 ± 0.1CTSFarrell and Newton, 1966RDSH
7.96EICrable and Kearns, 1962RDSH
7.74PEPalmer, Moyes, et al., 1979Vertical value; LLK
7.60PEStreets, Hall, et al., 1972Vertical value; LLK

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

Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, NIST Free Links, 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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Mass spectrum
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Additional Data

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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, 2010
NIST MS number 374679

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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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UVVis spectrum
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Additional Data

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Source Eggers and Schiebe, 1966
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 19781
Instrument Unicam SP 500
Melting point 63-64

Gas Chromatography

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

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryVF-5MS1303.Todua, 201130. m/0.25 mm/0.25 «mu»m, He; Tstart: 60. C; Tend: 270. C

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, Gas Chromatography, NIST Free Links, 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 «pi» 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]

Todua, 2011
Todua, N.G., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2011. [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, Gas Chromatography, NIST Free Links, References