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1,4-Benzenediamine

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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

Quantity Value Units Method Reference Comment
Deltafsolid6.3kJ/molCcbKunyavskaya, Karyakin, et al., 1973see Karyakin, Rabinovich, et al., 1978; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-3511. ± 3.kJ/molCcbKunyavskaya, Karyakin, et al., 1973see Karyakin, Rabinovich, et al., 1978; ALS
Deltacsolid-3507.4 ± 0.63kJ/molCcbKibler and Hunt, 1949Reanalyzed by Cox and Pilcher, 1970, Original value = -3506.9 ± 0.63 kJ/mol; ALS
Deltacsolid-3509.3 ± 0.63kJ/molCcbSullivan, Kibler, et al., 1948ALS
Quantity Value Units Method Reference Comment
solid,1 bar149.70J/mol*KN/AKunyavskaya, Karyakin, et al., 1973DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
155.64300.Kunyavskaya, Karyakin, et al., 1973T = 20 to 300 K.; DH

Phase change data

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

Quantity Value Units Method Reference Comment
Tboil540.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus412.3KN/ABret-Dibat and Lichanot, 1989Crystal phase 1 phase; Uncertainty assigned by TRC = 0.5 K; TRC
Tfus415.7KN/ARai and Mandal, 1989Uncertainty assigned by TRC = 0.1 K; TRC
Tfus414.2KN/AKemula, Buchowski, et al., 1968Uncertainty assigned by TRC = 0.2 K; TRC
Tfus414.14KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.3 K; TRC
Tfus414.35KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Deltasub92.2 ± 0.2kJ/molCSabbah and Perez, 1997AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
24.900416.Rai and Mandal, 1990Temperature from graph.; DH
21.7412.3Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
59.8416.Rai and Mandal, 1990Temperature; DH

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
L - 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
IE (evaluated)6.87 ± 0.05eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)905.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity874.0kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
6.84PETsuji, Saito, et al., 1973LLK
7.16EIJohnstone and Mellon, 1973LLK
6.89 ± 0.03PIPotapov, Kardash, et al., 1972LLK
7.0 ± 0.1CTSFarrell and Newton, 1966RDSH
7.58EICrable and Kearns, 1962RDSH
7.15CTSBriegleb and Czekalla, 1959RDSH
7.34PECabelli, Cowley, et al., 1981Vertical value; LLK
7.61PEPalmer, Moyes, et al., 1979Vertical value; LLK
7.34PEStreets, Hall, et al., 1972Vertical value; LLK

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


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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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, 1998.
NIST MS number 291211

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

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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: 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 Johnson, 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. 19802
Instrument Unicam SP 500
Melting point 141.5-142

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]

Kibler and Hunt, 1949
Kibler, G.M.; Hunt, H., Heats of combustion. V. The heats of combustion of five nitrogen-containing compounds, J. Phys. Chem., 1949, 53, 955-956. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Sullivan, Kibler, et al., 1948
Sullivan, M.V.; Kibler, G.M.; Hunt, H., Heats of combustion of nitrogen containing compounds, Rpt. Tech. Memo. PUR-3 for USN Project SQUID Contract N6ori-104, Task Order No. 1 Designation No. NR 22 042 by Purdue University, Lafayette, IN, 1948, 1-46. [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]

Rai and Mandal, 1989
Rai, U.S.; Mandal, K.D., Chemistry of organic eutectics and 1:1 addition compound: p-phenylenediamine-catechol system, Thermochim. Acta, 1989, 138, 219. [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]

Witschonke, 1954
Witschonke, C.R., Freezing point and purity data for some organic compounds, Anal. Chem., 1954, 26, 562-4. [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]

Rai and Mandal, 1990
Rai, U.S.; Mandal, K.D., Chemistry of organic eutectics: p-phenylenediamine-m-nitrobenzoic acid system involving the 1:2 addition compound, Bull. Chem. Soc. Jpn., 1990, 63(5), 1496-1502. [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]

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]

Johnstone and Mellon, 1973
Johnstone, R.A.W.; Mellon, F.A., Effects of induction and resonance in the calculation of ionization potentials of substituted benzenes by perturbation molecular orbital theory, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 36. [all data]

Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I., Photoionization of heteroaromatic compounds, Khim. Vys. Energ., 1972, 6, 392. [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]

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

Cabelli, Cowley, et al., 1981
Cabelli, D.E.; Cowley, A.H.; Dewar, M.J.S., UPE studies of conjugation involving group 5A elements. 1. Phenylphosphines, J. Am. Chem. Soc., 1981, 103, 3286. [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]

Johnson, 1966
Johnson, E.A., UV atlas of organic compounds, 1966, 2, D9/59. [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