1,3-Phenylenediamine
- Formula: C6H8N2
- Molecular weight: 108.1411
- IUPAC Standard InChIKey: WZCQRUWWHSTZEM-UHFFFAOYSA-N
- 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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Phase change data
Go To: Top, 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:
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 |
---|---|---|---|---|---|
Tboil | 556.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 337. | K | N/A | Lesbats and Lichanot, 1987 | DH |
Tfus | 335. | K | N/A | Bret-Dibat and Lichanot, 1989 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 339.1 | K | N/A | Rabinovich, Nistratov, et al., 1984 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 90.4 ± 0.4 | kJ/mol | C | Sabbah and Perez, 1997 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
63.7 | 387. | A | Stephenson and Malanowski, 1987 | Based on data from 372. to 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 to 558.7 | 5.11734 | 2635.233 | -43.185 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
15.570 | 339.1 | Rabinovich, Karyakin, et al., 1984 | DH |
15.4 | 335.5 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
45.92 | 339.1 | Rabinovich, Karyakin, et al., 1984 | DH |
Gas phase ion energetics data
Go To: Top, 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
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) | 929.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 899.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.14 | PI | Pykhtina, Cherednichenko, et al., 1974 | LLK |
7.44 | PE | Tsuji, Saito, et al., 1973 | LLK |
7.5 ± 0.1 | CTS | Farrell and Newton, 1966 | RDSH |
7.96 | EI | Crable and Kearns, 1962 | RDSH |
7.74 | PE | Palmer, Moyes, et al., 1979 | Vertical value; LLK |
7.60 | PE | Streets, Hall, et al., 1972 | Vertical value; LLK |
References
Go To: Top, 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.
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]
Lesbats and Lichanot, 1987
Lesbats, C.; Lichanot, A.,
Capacites calorifiques de durcisseurs amines et resines epoxydes,
Thermochim. Acta, 1987, 109, 317-329. [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]
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 the condensation of o-phthalic acid dinitrile with m-phenylenediamine, Izv. Akad. Nauk SSSR,
Ser. Khim., 1984, (4), 779-787. [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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature 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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