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

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

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 thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, 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]

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 thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  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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