Benzenamine, 4,4'-methylenebis-

• Formula: C₁₃H₁₄N₂
• Molecular weight: 198.2637
• IUPAC Standard InChI: InChI=1S/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2 Copy

  
• IUPAC Standard InChIKey: YBRVSVVVWCFQMG-UHFFFAOYSA-N Copy
• CAS Registry Number: 101-77-9
• 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: Aniline, 4,4'-methylenedi-; p,p'-Diaminodiphenylmethane; p,p'-Methylenedianiline; Bis(p-aminophenyl)methane; Bis(4-aminophenyl)methane; Diaminodiphenylmethane; Dianilinemethane; Epicure DDM; Epikure DDM; HT 972; Jeffamine AP-20; Methylenebis[aniline]; Methylenedianiline; Tonox; 4,4'-Diaminodiphenylmethane; 4,4'-Diphenylmethanediamine; 4,4'-Methylenebis[aniline]; 4,4'-Methylenedianiline; p-Toluidine, α-(p-aminophenyl)-; p,p'-Diaminodifenylmethan; Bis-p-aminofenylmethan; Di(4-aminophenyl)methane; DADPM; DDM; MDA; NCI-C54604; 4-(4-Aminobenzyl)aniline; 4,4'-Diaminodiphenylmethan; Ancamine TL; Araldite hardener 972; Curithane; 4,4'-Methylenebis(benzeneamine); 4,4-Methylenedianiline; Sumicure M; UN 2651; Bis(aminophenyl)methane; 4,4'-Methylenedibenzenamine; Dianiline, 4,4'-methylene-; NSC 4709
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• Information on this page:
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

Constant pressure heat capacity of solid

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry 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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

Appearance energy determinations

References

Go To: Top, Condensed phase thermochemistry 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.

Zalykin and Strepikheev, 1966
Zalykin, A.A.; Strepikheev, Yu.A., Certain physicochemical constants of 4,4'-diaminodiphenylmethane and diphenylmethane 4,4'diisocyanate, J. Appl. Chem. USSR (Engl. Transl.), 1966, 39, 2448, In original 2607. [all data]

Kishore and Santhanalakshmi, 1983
Kishore, K.; Santhanalakshmi, K.N., A thermochemical study on the reactions of aniline with formaldehyde in the presence of acid medium, Thermochim. Acta, 1983, 68, 59-74. [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]

Marchidan and Ciopec, 1978
Marchidan, D.I.; Ciopec, M., Relative enthalpies and related thermodynamic functions of some organic compounds by drop calorimetry, J. Therm. Anal., 1978, 14, 131-150. [all data]

Zalikin and Strepikheev, 1966
Zalikin, A.A.; Strepikheev, Yu.A., Some physicochemical constants of 4,4'-diaminodiphenylmethane and 4,4'-diphenylmethanediisocyanate, Zhur. Priklad. Khim., 1966, 39, 2607. [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]

Pignataro, Mancini, et al., 1972
Pignataro, S.; Mancini, V.; Innorta, G.; Distefano, G., Ionization energies and ring orbital interaction in diarylmethanes and diaryleth, Z. Naturforsch., 1972, 27, 534. [all data]

Innorta, Torroni, et al., 1973
Innorta, G.; Torroni, S.; Pignataro, S.; Mancini, V., The activation energy as guiding factor in the fragmentation of substituted diphenylmethanes, Org. Mass Spectrom., 1973, 7, 1399. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,solid	Constant pressure heat capacity of solid
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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