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
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• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Ion clustering data
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

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

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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 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

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT) $$ PURITY - ANALYTICAL; PERKIN-ELMER 180 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm^-1 resolution
• SOLUTION (10% IN CCl4 FOR 3800-1300, 2% IN CS2 FOR 1300-650, AND 10% IN CCl4 FOR 650-250 CM^-1) VERSUS SOLVENT; Not specified, most likely a grating or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas; HP-GC/MS/IRD

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

Marcus Y., 1986
Marcus Y., Entropies of tetrahedral M-phenyl species, J. Chem. Soc., Faraday Trans. 1, 1986, 82, 993-1006. [all data]

Dorofeeva O.V., 1997
Dorofeeva O.V., Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]

Puranik P.G., 1962
Puranik P.G., Vibrational spectra, potential constants, and thermodynamic properties of diphenylmethane, Proc. Indian Acad. Sci., 1962, A56, 233-238. [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]

Kortum and Dreesen, 1951
Kortum, G.; Dreesen, G., Uber die konstitutions-abhangigkeit der schwingungsstruktur im absoprtionsspektrum von aromatischen kohlenwasserstoffen, Chem. Ber., 1951, 84, 2, 182-203. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  S°gas	Entropy of gas at standard conditions
  T	Temperature
  ΔfH°gas	Enthalpy of formation of gas 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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