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 ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
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  • Gas Phase Kinetics Database
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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

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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Lee's RI, non-polar column, custom temperature program

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References

Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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]

Giumanini, Verardo, et al., 2001
Giumanini, A.G.; Verardo, G.; Soják, L.; Kubinec, R.; Perjéssy, A., Identification of mononitro and dinitro isomers of diphenylmethane by GC-FT-IR and GC-MS techniques, Ind. Eng. Chem. Res., 2001, 40, 6, 1449-1453, https://doi.org/10.1021/ie000667u . [all data]

Tudor, 1997
Tudor, E., Temperature dependence of the retention index for perfumery compounds on a SE-30 glass capillary column. I. Linear equations, J. Chromatogr. A, 1997, 779, 1-2, 287-297, https://doi.org/10.1016/S0021-9673(97)00453-6 . [all data]

van Haelst, van der Wielen, et al., 1996
van Haelst, Anniek G.; van der Wielen, Frans W.M.; Govers, Harrie A.J., Gas chromatographic determination of liquid vapour pressure and heat of vaporization of tetrachlorobenzyltoluenes, Journal of Chromatography A, 1996, 727, 2, 265-273, https://doi.org/10.1016/0021-9673(95)01146-3 . [all data]

Gerasimenko, Kirilenko, et al., 1981
Gerasimenko, V.A.; Kirilenko, A.V.; Nabivach, V.M., Capillary gas chromatography of aromatic compounds found in coal tar fractions, J. Chromatogr., 1981, 208, 1, 9-16, https://doi.org/10.1016/S0021-9673(00)87953-4 . [all data]

Shlyakhov, Anvaer, et al., 1975
Shlyakhov, A.F.; Anvaer, B.I.; Zolotareva, O.V.; Romina, N.N.; Novikova, N.V.; Koreshkova, R.I., On the possibility of group indentification of hydrocarbons by gas chromatography from temperature coefficients of retention indices, Zh. Anal. Khim., 1975, 30, 788-792. [all data]

Toda, Mihara, et al., 1983
Toda, H.; Mihara, S.; Umano, K.; Shibamoto, T., Photochemical studies on jasmin oil, J. Agric. Food Chem., 1983, 31, 3, 554-558, https://doi.org/10.1021/jf00117a022 . [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [all data]

Shapi and Hesso, 1990
Shapi, M.M.; Hesso, A., Thermal decomposition of polystyrene volatile compounds from large-scale pyrolysis, J. Anal. Appl. Pyrolysis, 1990, 18, 2, 143-161, https://doi.org/10.1016/0165-2370(90)80004-8 . [all data]

Helmig, Bocquet, et al., 2004
Helmig, D.; Bocquet, F.; Pollmann, J.; Revermann, T., Analytical techniques for sesquiterpene emission rate studies in vegetation enclosure experiments, Atmos. Environ., 2004, 38, 4, 557-572, https://doi.org/10.1016/j.atmosenv.2003.10.012 . [all data]

Nabivach and Gerasimenko, 1996
Nabivach, V.M.; Gerasimenko, V.A., Gas chromatographic retention characteristics of bicyclic aromatic hydrocarbons, Coke and Chemistry (Rus), 1996, 6, 27-31. [all data]

Elizalde-González, Hutfliess, et al., 1996
Elizalde-González, M.P.; Hutfliess, M.; Hedden, K., Retention index system, adsorption characteristics, and sructure correlations of polycyclic aromatic hydrocarbons in fuels, J. Hi. Res. Chromatogr., 1996, 19, 6, 345-352, https://doi.org/10.1002/jhrc.1240190608 . [all data]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [all data]

Grigor'ev, Bozhko, et al., 2009
Grigor'ev, A.M.; Bozhko, E.S.; Rudakova, L.V., Use of correlation between retention indices on low-polarity phases for screening comp-lex mixtures by gas chromatography-mass spectrometry, Rus. J. Anal. Chem., 2009, 64, 2, 140-143, https://doi.org/10.1134/S1061934809020087 . [all data]

Helmig, Revermann, et al., 2003
Helmig, D.; Revermann, T.; Pollmann, J.; Kaltschmidt, O.; Hernández, A.J.; Bocquet, F.; David, D., Calibration system and analytical considerations for quantitative sesquiterpene measurements in air, J. Chromatogr. A, 2003, 1002, 1-2, 193-211, https://doi.org/10.1016/S0021-9673(03)00619-8 . [all data]

Peng, 1996
Peng, C.T., Gas chromatographic identification of aromatic hydrocarbons in Liquid Scintillation Spectrometry, Cook, G.T.; Harkness, D.D.; MacKenzie, A.B.; Miller, B.F.; Scott, E.M., ed(s)., 1996, 221-232. [all data]

Zenkevich, 1994
Zenkevich, I.G., Contemporary State of Informational Maintenance for Gas Chromatographic Identification of Chlorinated Polycyclic Aromatic Compounds, Zh. Ecol. Khim., 1994, 3, 2, 111-119. [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Wang, Hou, et al., 2007
Wang, G.; Hou, Z.; Sun, Y.; Liu, Y.; Xie, B.; Liu, S., Investigation of pyrolysis behavior of fenoxycarb using PY-GC-MS assisted with chemometric methods, Chem. Anal., 2007, 52, 141-156. [all data]

Shao, Wang, et al., 2006
Shao, X.; Wang, G.; Sun, Y.; Zhang, R.; Xie, K.; Liu, H., Determination and Characterization of the Pyrolysis Products of Isoprocarb by GC-MS, J. Chromatogr. Sci., 2006, 44, 3, 141-147, https://doi.org/10.1093/chromsci/44.3.141 . [all data]

Marynowski, Pieta, et al., 2004
Marynowski, L.; Pieta, M.; Janeczek, J., Composition and source of polycyclic aromatic compounds in deposited dust from selected sites around the Upper Silesia, Poland, Geol. Q., 2004, 48, 2, 169-180. [all data]

Piao, Chu, et al., 1999
Piao, M.; Chu, S.; Zheng, M.; Xu, X., Characterization of the combustion products of polyethylene, Chemosphere, 1999, 39, 9, 1497-1512, https://doi.org/10.1016/S0045-6535(99)00054-5 . [all data]

Schwarzbauer, Franke, et al., 1999
Schwarzbauer, J.; Franke, S.; Francke, W., Chlorinated di- and triphenylmethanes in sediments of the Mulde and Elbe rivers. Part IV of organic compounds as contaminants of the Elbe river and its tributaries, Fresenius J. Anal. Chem., 1999, 365, 6, 529-536, https://doi.org/10.1007/s002160051517 . [all data]

Bundt, Herbel, et al., 1991
Bundt, J.; Herbel, W.; Steinhart, H.; Franke, S.; Francke, W., Structure-type separation of diesel fuels by solid phase extraction and identification of the two- and three-ring aromatics by capillary GC-mass spectrometry, J. Hi. Res. Chromatogr., 1991, 14, 2, 91-98, https://doi.org/10.1002/jhrc.1240140205 . [all data]

Guillén, Blanco, et al., 1989
Guillén, M.D.; Blanco, J.; Bermejo, J.; Blanco, C.G., Temperature programmed retention indices of some PAHs on Capillary columns coated with OV-1701 and SE-54, J. Hi. Res. Chromatogr., 1989, 12, 8, 552-554, https://doi.org/10.1002/jhrc.1240120816 . [all data]

Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M., Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons, Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043 . [all data]

Notes

Go To: Top, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  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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