1,2-Benzenediamine
- Formula: C6H8N2
- Molecular weight: 108.1411
- IUPAC Standard InChIKey: GEYOCULIXLDCMW-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - 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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Condensed phase thermochemistry data
Go To: Top, 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 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 |
---|---|---|---|---|---|
ΔfH°solid | 39.1 ± 5.7 | kJ/mol | Ccb | Contineanu, Wagner, et al., 1982 | ALS |
ΔfH°solid | 0.0 | kJ/mol | Ccb | Kunyavskaya, Karyakin, et al., 1973 | see Karyakin, Rabinovich, et al., 1978; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -3543.5 ± 5.7 | kJ/mol | Ccb | Contineanu, Wagner, et al., 1982 | ALS |
ΔcH°solid | -3504. ± 3. | kJ/mol | Ccb | Kunyavskaya, Karyakin, et al., 1973 | see Karyakin, Rabinovich, et al., 1978; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 152.09 | J/mol*K | N/A | Kunyavskaya, Karyakin, et al., 1973 | DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
150.82 | 298.15 | Bret-Dibat and Lichanot, 1989 | T = 200 to 500 K. Cp(c) = 135.620 + 0.5717t + 1.1893x10-3t2 + 1.0768x10-5t3 J/mol*K (t/°C). Cp value calculated from equation.; DH |
162.13 | 300. | Kunyavskaya, Karyakin, et al., 1973 | T = 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
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 |
---|---|---|---|---|---|
Tboil | 530.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 460.2 | K | N/A | Richards and Mathews, 1908 | Uncertainty assigned by TRC = 1. K; TRC |
Tboil | 530.15 | K | N/A | Perkin, 1896 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 373.9 | K | N/A | Bret-Dibat and Lichanot, 1989, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 377. | K | N/A | Kemula, Buchowski, et al., 1968 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 85.5 ± 0.3 | kJ/mol | C | Sabbah and Perez, 1997 | AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
23.100 | 373.85 | Bret-Dibat and Lichanot, 1989 | DH |
23.1 | 373.9 | Lee, Chang, et al., 1997 | See also Bret-Dibat and Lichanot, 1989.; AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
62. | 373.85 | Bret-Dibat and Lichanot, 1989 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 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) | 896.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 865.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.2 | PE | Tsuji, Saito, et al., 1973 | LLK |
7.4 ± 0.1 | CTS | Farrell and Newton, 1966 | RDSH |
7.36 | CTS | Kinoshita, 1962 | RDSH |
8.00 | EI | Crable and Kearns, 1962 | RDSH |
7.45 | CTS | Briegleb and Czekalla, 1959 | RDSH |
7.78 | PE | Palmer, Moyes, et al., 1979 | Vertical value; LLK |
7.69 | PE | Streets, Hall, et al., 1972 | Vertical 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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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 |
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.
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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Source | Lang (editor), 1969 |
---|---|
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. 19050 |
Instrument | Unicam SP 800 |
Melting point | 102 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, 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]
Lang (editor), 1969
Lang (editor), L.,
Absorption Spectra in the Ultraviolet and Visible Region, 1969, 12, 85. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, 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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