1,4-Benzenediamine

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

  
• IUPAC Standard InChIKey: CBCKQZAAMUWICA-UHFFFAOYSA-N Copy
• CAS Registry Number: 106-50-3
• 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.
• Other names: p-Aminoaniline; p-Benzenediamine; p-Diaminobenzene; p-Phenylenediamine; Benzofur D; BASF Ursol D; C.I. Developer 13; C.I. Oxidation Base 10; C.I. 76060; Developer PF; Durafur Black R; Fouramine D; Fourrine D; Fourrine 1; Fur Black 41867; Fur Brown 41866; Fur Yellow; Furro D; Futramine D; Nako H; Orsin; Pelagol D; Pelagol DR; Pelagol Grey D; Peltol D; Renal PF; Santoflex LC; Tertral D; Ursol D; Zoba Black D; 1,4-Diaminobenzene; 1,4-Phenylenediamine; 4-Aminoaniline; Developer 13; Fenylenodwuamina; Oxidation base 10; Phenylenediamine, para; PARA; PPD; Santoflex IC; USAF EK-394; p-Fenylendiamin; Paraphenylen-diamine; Rodol D; UN 1673; Vulkanox 4020; Aminogen II; NSC 4777
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Condensed phase thermochemistry data

Go To: Top, Phase change data, Gas phase ion energetics data, 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:
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

Go To: Top, Condensed phase thermochemistry data, Phase change data, References, Notes

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)

Ionization energy determinations

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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 π energy levels of aminobenzenes studied by photoelectron spectroscopy, Chem. Phys. Lett., 1972, 17, 90. [all data]

Notes

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• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  IE (evaluated)	Recommended ionization energy
  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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