Diphenylmethane

• Formula: C₁₃H₁₂
• Molecular weight: 168.2344
• IUPAC Standard InChI: InChI=1S/C13H12/c1-3-7-12(8-4-1)11-13-9-5-2-6-10-13/h1-10H,11H2 Copy

  
• IUPAC Standard InChIKey: CZZYITDELCSZES-UHFFFAOYSA-N Copy
• CAS Registry Number: 101-81-5
• 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: Benzene, 1,1'-methylenebis-; Methane, diphenyl-; Benzene, (phenylmethyl)-; Benzylbenzene; Ditan; Ditane; Benzene, benzyl-; Toluene, α-phenyl-; 1,1'-Dimethylenebis(benzene); NSC 4708
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• 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:
DRB - Donald R. Burgess, Jr.
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

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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

C₁₃H₁₁^- +  =

By formula: C₁₃H₁₁^- + H⁺ = C₁₃H₁₂

 +  = ( • )

By formula: Cl^- + C₁₃H₁₂ = (Cl^- • C₁₃H₁₂)

Free energy of reaction

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₁₃H₁₁^- +  =

By formula: C₁₃H₁₁^- + H⁺ = C₁₃H₁₂

References

Go To: Top, Condensed phase thermochemistry 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.

Roux, Temprado, et al., 2008
Roux, M.V.; Temprado, M.; Chickos, J.S.; Nagano, Y., Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons, J. Phys. Chem. Ref. Data, 2008, 37, 4, 1855-1996. [all data]

Steele, Chirico, et al., 1995
Steele, W.V.; Chirico, R.D.; Smith, N.K., The standard enthalpies of formation of 2-methylbiphenyl and diphenylmethane, J. Chem. Thermodyn., 1995, 27, 671-678. [all data]

Parks and Mosley, 1950
Parks, G.S.; Mosley, J.R., Redetermination of the heat of combustion of diphenylmethane, J. Am. Chem. Soc., 1950, 72, 1850. [all data]

Parks, West, et al., 1946
Parks, G.S.; West, T.J.; Naylor, B.F.; Fujii, P.S.; McClaine, L.A., Thermal data on organic compounds. XXIII. Modern combustion data for fourteen hydrocarbons and five polyhydroxy alcohols, J. Am. Chem. Soc., 1946, 68, 2524-2527. [all data]

Schmidlin, 1906
Schmidlin, M.J., Recherches chimiques et thermochimiques sur la constitution des rosanilines, Ann. Chim. Phys., 1906, 1, 195-256. [all data]

Serijan and Wise, 1951
Serijan, K.T.; Wise, P.H., Dicyclic hydrocarbons. III. Diphenyl- and dicyclohexylalkanes through C₁₅, J. Am. Chem. Soc., 1951, 73, 4766-4769. [all data]

Wise, Serijan, et al., 1951
Wise, C.H.; Serijan, K.T.; Goodman, I.A., NACA Technical Report 1003, NACA Technical Report 1003, 1951, 1-10. [all data]

Coops, Mulder, et al., 1946
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J., The heats of combustion of a number of hydrocarbons, Rec. Trav. Chim. Pays/Bas, 1946, 65, 128. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Huffman, Parks, et al., 1930
Huffman, H.M.; Parks, G.S.; Daniels, A.C., Thermal data on organic compounds. VII. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons, J. Am. Chem. Soc., 1930, 52, 1547-1558. [all data]

Duff and Everett, 1956
Duff, G.M.; Everett, D.H., The heat capacity of the system benzene + diphenylmethane, Trans. Faraday Soc., 1956, 52, 753-763. [all data]

Kurbatov, 1950
Kurbatov, V.Ya., Specific heats of liquids. III. Specific heat of hydrocarbons with several noncondensed rings, Zhur. Obshch. Khim., 1950, 20, 1139-1144. [all data]

Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H., Thermal energy studies. I. Phenyl derivatives of methane, ethane and some related compounds. J. Am. Chem. Soc., 1931, 53, 3644-3660. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [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]

Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G., Electron capture detection of aromatic hydrocarbons, J. Chromatogr. Sci., 1981, 206, 511. [all data]

Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E., Experimental Determination of Electron Affinities of Organic Molecules, Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]

Terlouw, Heerma, et al., 1974
Terlouw, J.K.; Heerma, W.; Frintrop, P.C.M.; Dijkstra, G.; Meinema, H.A., Electron-impact induced fragmentation of some heterocyclic-tin compounds, J. Organomet. Chem., 1974, 64, 205. [all data]

Bohlmann, Koppel, et al., 1974
Bohlmann, F.; Koppel, C.; Muller, B.; Schwarz, H.; Weyerstahl, P., Massenspektrometrische Untersuchung isomerer Kohlenwasserstoffe: Struktur und Bildungsenthalpie stabiler (C₁₃H₁₁⁺) Ionen, Tetrahedron, 1974, 30, 1011. [all data]

Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I., Photoionization of heteroaromatic compounds, Khim. Vys. Energ., 1972, 6, 392. [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]

Distefano, Pignataro, et al., 1976
Distefano, G.; Pignataro, S.; Szepes, L.; Borossay, J., Photoelectron spectroscopy study of the triphenyl derivatives of the group IV elements, J. Organomet. Chem., 1976, 104, 173. [all data]

Eaton and Traylor, 1974
Eaton, D.F.; Traylor, T.G., Distortional stabilization in phenyl participations, J. Am. Chem. Soc., 1974, 96, 7109. [all data]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part 2. Phenylethylenes, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 196. [all data]

Pignataro, Mancini, et al., 1971
Pignataro, S.; Mancini, V.; Ridyard, J.N.A.; Lempka, H.J., Photoelectron energy spectra of molecules having classically non-conjugated π-systems, Chem. Commun., 1971, 142. [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]

Rapp, Staab, et al., 1970
Rapp, U.; Staab, H.A.; Wunsche, C., Skelettumlagerungen unter Elektronenbeschuss-IV: zur Struktur der C₁₃H₉- und C₁₂H₉N-Ionen bei Benzylidenaminobenztriazolen, Org. Mass Spectrom., 1970, 3, 45. [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,solid	Constant pressure heat capacity of solid
  EA	Electron affinity
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  T	Temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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