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
- IUPAC Standard InChIKey: YBRVSVVVWCFQMG-UHFFFAOYSA-N
- 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
View 3d structure (requires JavaScript / HTML 5) - 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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Reaction thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
=
By formula: C13H14N2 = C13H14N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 14.415 ± 0.010 | kcal/mol | Kin | Santhanalakshmi, 1988 | liquid phase; solvent: Aqueous |
Gas phase ion energetics data
Go To: Top, Reaction 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
| IE (eV) | Method | Reference |
|---|---|---|
| 7.20 | PI | Pykhtina, Cherednichenko, et al., 1974 |
| 7.75 ± 0.05 | EI | Pignataro, Mancini, et al., 1972 |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C7H8N+ | 10.6 ± 0.1 | ? | EI | Innorta, Torroni, et al., 1973 | |
| C13H12N+ | 10.7 ± 0.1 | NH2 | EI | Innorta, Torroni, et al., 1973 |
References
Go To: Top, Reaction 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.
Santhanalakshmi, 1988
Santhanalakshmi, J.,
A thermochemical kinetic study of interconversion reactions of aniline-formaldehyde products,
Thermochim. Acta, 1988, 127, 369-375. [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, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.