4,4'-Dimethylbiphenyl

• Formula: C₁₄H₁₄
• Molecular weight: 182.2610
• IUPAC Standard InChI: InChI=1S/C14H14/c1-11-3-7-13(8-4-11)14-9-5-12(2)6-10-14/h3-10H,1-2H3 Copy

  
• IUPAC Standard InChIKey: RZTDESRVPFKCBH-UHFFFAOYSA-N Copy
• CAS Registry Number: 613-33-2
• 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: 1,1'-Biphenyl, 4,4'-dimethyl-; p,p'-Bitolyl; Bi-p-tolyl; Di-p-tolyl; 4,4'-Bitolyl; 4,4'-Dimethyl-1,1'-biphenyl; 4,4'-Dimethyldiphenyl; 4,4'-Ditolyl; 1-Methyl-4-(4'-methylphenyl)benzene; p,p'-Bitoluene; p,p'-Ditolyl; Biphenyl, 4,4'-dimethyl-; NSC 90464; 1-Methyl-4-(4-methylphenyl)benzene; Diphenyl, 4,4'-dimethyl
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.

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 as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

Appearance energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% CCl4 FOR 3800-1330, 10% CS2 FOR 1330-400 CM^-1); BECKMAN IR-9 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm^-1 resolution

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

• gas

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

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, isothermal

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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, polar column, temperature ramp

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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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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, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

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

Ribeiro da Silva, Matos, et al., 1997
Ribeiro da Silva, M.A.V.; Matos, M.A.R.; do Rio, C.M.A.; Morais, V.M.F., Thermochemical and theoretical studies of 4-methylbiphenyl, 4,4'-dimethylbiphenyl, 4,4'-dimethyl-2,2'-bipyridine, J. Chem. Soc. Farad. Trans, 1997, 93, 3061. [all data]

Brull, 1935
Brull, L., Sui calori di combustione di alcuni derivati del bifenil, Gazz. Chim. Ital., 1935, 65, 19-28. [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]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Blades, Blades, et al., 1954
Blades, H.; Blades, A.; Steacie, E.W.R., The Kinetics of Pyrolysis of Toluene, Can. J. Chem., 1954, 32, 298-311. [all data]

Ullmann, 1904
Ullmann, F., Justus Liebigs Ann. Chem., 1904, 332, 38. [all data]

Schultz, 1881
Schultz, G., Justus Liebigs Ann. Chem., 1881, 207, 361. [all data]

Carnelley, 1877
Carnelley, T., J. Chem. Soc., 1877, 32, 653. [all data]

Ribeiro da Silva, Matos, et al., 1997, 2
Ribeiro da Silva, Manuel A.V.; Matos, Agostinha R.; do Rio, Carolina M.A.; Morais, Victor M.F., Thermochemical and theoretical studies of 4-methylbiphenyl, 4,4´-dimethylbiphenyl, 4,4´-dimethyl-2,2´-bipyridine, Faraday Trans., 1997, 93, 17, 3061-3065, https://doi.org/10.1039/a701769c . [all data]

Loudon and Mazengo, 1974
Loudon, A.G.; Mazengo, R.Z., Steric strain and electron-impact. The behaviour of some n, n'-dimethyl- 1,1-binaphthyls, some n, n'-dimethylbiphenyls and model compounds, Org. Mass Spectrom., 1974, 8, 179. [all data]

Ando and Tokura, 1958
Ando, T.; Tokura, N., Benzylation of acetylene. II. On the structure and oxidation of 3-benzyl-3,4-diphenyl-1-butyne, Bull. Chem. Soc. Jpn., 1958, 31, 351-355. [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]

Kríz, Popl, et al., 1974
Kríz, J.; Popl, M.; Mostecký, J., Retention indices of biphenyls and diphenylalkanes, J. Chromatogr., 1974, 97, 1, 3-13, https://doi.org/10.1016/S0021-9673(01)97577-6 . [all data]

Song, Lai, et al., 2003
Song, C.; Lai, W.-C.; Madhusudan Reddy, K.; Wei, B., Chapter 7. Temperature-programmed retention indices for GC and GC-MS of hydrocarbon fuels and simulated distillation GC of heavy oils in Analytical advances for hydrocarbon research, Hsu,C.S., ed(s)., Kluwer Academic/Plenum Publishers, New York, 2003, 147-193. [all data]

Lai and Song, 1995
Lai, W.-C.; Song, C., Temperature-programmed retention indices for g.c. and g.c.-m.s. analysis of coal- and petroleum-derived liquid fuels, Fuel, 1995, 74, 10, 1436-1451, https://doi.org/10.1016/0016-2361(95)00108-H . [all data]

Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

Beernaert, 1979
Beernaert, H., Gas Chromatographic Analysis of Polyclylic Aromatic Hydrocarbons, J. Chromatogr., 1979, 173, 1, 109-118, https://doi.org/10.1016/S0021-9673(01)80450-7 . [all data]

Chung, 1999
Chung, H.Y., Volatile components in crabmeats of Charybdis feriatus, J. Agric. Food Chem., 1999, 47, 6, 2280-2287, https://doi.org/10.1021/jf981027t . [all data]

Ferrand, 1962
Ferrand, R., Gas phase chromatography using retention indices for the analysis of tars and their hydrogenation products, Journees internationales d'etude des methodes de separation immediate at de chromatographie; Org. sur l'initiative du IX., 1962, 132-140. [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]

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]

Durlak, Biswas, et al., 1998
Durlak, S.K.; Biswas, P.; Shi, J.; Bernhard, M.J., Characterization of polycyclic aromatic hydrocarbon particulate and gaseous emissions from polystyrene combustion, Environ. Sci. Technol., 1998, 32, 15, 2301-2307, https://doi.org/10.1021/es9709031 . [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]

Fuentes, Font, et al., 2007
Fuentes, M.J.; Font, R.; Gomez-Rico, M.F.; Martin-Gullon, I., Pyrolysis and combustion of waste lubricant oil from diesel cars: Decomposition and pollutants, J. Anal. Appl. Pyrolysis, 2007, 79, 1-2, 215-226, https://doi.org/10.1016/j.jaap.2006.12.004 . [all data]

Naikwadi, Charbonneau, et al., 1987
Naikwadi, K.P.; Charbonneau, G.M.; Karasek, F.W.; Clement, R.E., Separation and Identification of Organic Compounds in Air Particulate Extracts by High-Performance Liquid Chromatography and Gas Chromatography-Mass Spectrometry, J. Chromatogr., 1987, 398, 227-237, https://doi.org/10.1016/S0021-9673(01)96508-2 . [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔsubH°	Enthalpy of sublimation at standard conditions

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