Benzenamine, 4,4'-methylenebis-

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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

Quantity Value Units Method Reference Comment
Δcliquid-1721. ± 4.kcal/molCcbZalykin and Strepikheev, 1966ALS
Quantity Value Units Method Reference Comment
Δfsolid  CcbKishore and Santhanalakshmi, 1983uncertain value: 19.58 ± 0.05 kcal/mol; Data origin uncertain; ALS
Δfsolid  CcbKishore and Santhanalakshmi, 1983uncertain value: 19.70 ± 0.05 kcal/mol; Data origin uncertain; ALS
Quantity Value Units Method Reference Comment
Δcsolid  CcbKishore and Santhanalakshmi, 1983uncertain value: -2089.7 ± 1.6 kcal/mol; Data origin uncertain; ALS
Δcsolid  CcbKishore and Santhanalakshmi, 1983uncertain value: -2090.1 ± 1.8 kcal/mol; Data origin uncertain; ALS

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
64.75298.Lesbats and Lichanot, 1987T = 250 to 400 K.; DH
15.9298.Marchidan and Ciopec, 1978T = 298 to 469 K. Data seem odd; values for solid increase from 66.5 to 606.3 J/mol*K at 370 K to 463.2 J/mol*K at 470 K.; DH
54.30388.Zalikin and Strepikheev, 1966T = 110 to 120°C, mean value.; 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:
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tfus366.KN/ALesbats and Lichanot, 1987DH
Tfus363.8KN/AMarchidan and Ciopec, 1978, 2Uncertainty assigned by TRC = 0.5 K; TRC
Tfus363.7KN/AMarchidan and Ciopec, 1978, 3Uncertainty assigned by TRC = 0.5 K; TRC
Tfus366.KN/AZalikin and Strepikheev, 1966DH

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
26.12358.AStephenson and Malanowski, 1987Based on data from 343. to 393. K.; AC
23.4501.AStephenson and Malanowski, 1987Based on data from 486. to 545. K.; AC
21.3 ± 0.5471.VZalykin and Strepikheev, 1966ALS
24.04502.AZalikin and Strepikheev, 1966Based on data from 471. to 545. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
471. to 545.0.9374418.787-356.851Zalikin and Strepikheev, 1966Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
4.706362.7DSCKhimeche and Dahmani, 2006AC
2.21363.7N/ADomalski and Hearing, 1996AC
2.205363.7N/AMarchidan and Ciopec, 1978DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
6.07363.7Marchidan and Ciopec, 1978DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction 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 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

N,N'-Diphenylmethylenediamine = Benzenamine, 4,4'-methylenebis-

By formula: C13H14N2 = C13H14N2

Quantity Value Units Method Reference Comment
Δr14.415 ± 0.010kcal/molKinSanthanalakshmi, 1988liquid phase; solvent: Aqueous

Gas phase ion energetics 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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV) Method Reference
7.20PIPykhtina, Cherednichenko, et al., 1974
7.75 ± 0.05EIPignataro, Mancini, et al., 1972

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H8N+10.6 ± 0.1?EIInnorta, Torroni, et al., 1973 
C13H12N+10.7 ± 0.1NH2EIInnorta, Torroni, et al., 1973 

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, 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.

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]

Marchidan and Ciopec, 1978, 2
Marchidan, D.I.; Ciopec, M., Relative enthalpies and related thermodynamic functions of some organic compounds by drop calorimetry, J. Therm. Anal., 1978, 14, 131-49. [all data]

Marchidan and Ciopec, 1978, 3
Marchidan, D.I.; Ciopec, M., Thermodynamic properties of maleic, trimellitic and pryomellitic anhydrides, Rev. Roum. Chim., 1978, 23, 1, 19-20. [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]

Khimeche and Dahmani, 2006
Khimeche, K.; Dahmani, A., Determination by DSC of solid--liquid diagrams for polyaromatic -- 4,4'diaminodiphenylmethane binary systems, J Therm Anal Calorim, 2006, 84, 1, 47-52, https://doi.org/10.1007/s10973-005-7167-9 . [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]

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

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