3,3'-Dimethylbiphenyl
- Formula: C14H14
- Molecular weight: 182.2610
- IUPAC Standard InChI: InChI=1S/C14H14/c1-11-5-3-7-13(9-11)14-8-4-6-12(2)10-14/h3-10H,1-2H3
- IUPAC Standard InChIKey: GVEDOIATHPCYGS-UHFFFAOYSA-N
- CAS Registry Number: 612-75-9
- 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, 3,3'-dimethyl-; m,m'-Bitolyl; 3,3'-Ditolyl; 3,3'-Dimethyldiphenyl; 3,3-Dimethyldiphenyl; 1-Methyl-3-(3'-methylphenyl)benzene; Biphenyl, 3,3'-dimethyl-; 3,3'-dimethyl-1,1'-biphenyl; Diphenyl, 3,3'-dimethyl
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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, References, Notes
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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 559. | K | N/A | Blades, Blades, et al., 1954 | Uncertainty assigned by TRC = 8. K; TRC |
| Tboil | 556. | K | N/A | Brull, 1935 | Uncertainty assigned by TRC = 3. K; TRC |
| Tboil | 559. | K | N/A | Mayer and Freitak, 1921 | Uncertainty assigned by TRC = 3. K; TRC |
| Tboil | 561. | K | N/A | Perrier, 1892 | Uncertainty assigned by TRC = 5. K; TRC |
| Tboil | 562. | K | N/A | Stolle, 1888 | Uncertainty assigned by TRC = 5. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 278. | K | N/A | Castro, Andrews, et al., 1958 | Uncertainty assigned by TRC = 3. K; TRC |
| Tfus | 282.4 | K | N/A | Johnson, 1957 | Uncertainty assigned by TRC = 1.5 K; TRC |
| Tfus | 279. | K | N/A | Schultz, Rohde, et al., 1907 | Uncertainty assigned by TRC = 3. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 71.9 | kJ/mol | A | Stephenson and Malanowski, 1987 | Based on data from 288. to 308. K. See also Pribilová and Pouchlý, 1974.; AC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 71.9 | kJ/mol | ME | Pribilová and Pouchlý, 1974 | Based on data from 288. to 308. K.; AC |
Reduced pressure boiling point
| Tboil (K) | Pressure (bar) | Reference | Comment |
|---|---|---|---|
| 559.2 | 0.951 | Aldrich Chemical Company Inc., 1990 | BS |
| 423.2 | 0.024 | Weast and Grasselli, 1989 | BS |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, References, Notes
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
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.70 ± 0.05 | EI | Loudon and Mazengo, 1974 | LLK |
| 7.85 ± 0.02 | PE | Maier and Turner, 1972 | LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C13H11+ | 13.4 ± 0.2 | CH3 | EI | Loudon and Mazengo, 1974 | LLK |
| C14H13+ | 13.0 ± 0.2 | H | EI | Loudon and Mazengo, 1974 | LLK |
Gas Chromatography
Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes
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
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | OV-1 | 160. | 1591. | Zhang, Chen, et al., 1997 | 25. m/0.2 mm/0.33 μm, N2 |
Kovats' RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | SP-1000 | 185. | 2254. | Kríz, Popl, et al., 1974 | N2; Column length: 50. m; Column diameter: 0.25 mm |
| Capillary | SP-1000 | 200. | 2212. | Kríz, Popl, et al., 1974 | N2; Column length: 50. m; Column diameter: 0.25 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 1589.0 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1588.6 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; Tend: 310. C |
| Capillary | DB-5 | 1580.2 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1589.0 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1594.2 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1589.0 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1588.6 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; Tend: 310. C |
| Capillary | DB-5 | 1580.2 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1589. | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1594.2 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1597. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
| Capillary | SE-52 | 1574. | Beernaert, 1979 | He, 50. C @ 5. min, 6. K/min; Column length: 33.3 m; Column diameter: 0.50 mm; Tend: 320. C |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Supelcowax-10 | 2209. | Chung, Yung, et al., 2002 | 60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min |
| Capillary | Supelcowax-10 | 2209. | Chung, Yung, et al., 2001 | 60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min |
| Capillary | Supelcowax-10 | 2208. | Chung, 1999 | 60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min |
Normal alkane RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | Polydimethyl siloxane | 183. | 1580. | Ferrand, 1962 |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 MS | 1594. | Radulovic, Blagojevic, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
| Capillary | Ultra-1 | 1570. | Elizalde-González, Hutfliess, et al., 1996 | 50. m/0.2 mm/0.33 μm, H2, 3. K/min, 300. C @ 35. min; Tstart: 60. C |
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 271.27 | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
| Capillary | DB-5 | 270.79 | Tong, Centen, et al., 1985 | He, 4. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tstart: 90. C; Tend: 325. C |
| Capillary | SE-52 | 271.87 | Lee, Vassilaros, et al., 1979 | 12. m/0.3 mm/0.34 μm, He, 2. K/min; Tstart: 50. C; Tend: 250. C |
Lee's RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 271.87 | Tong, Centen, et al., 1985 | He; Column length: 30. m; Column diameter: 0.25 mm; Program: not specified |
References
Go To: Top, Phase change data, 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.
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]
Brull, 1935
Brull, L.,
Sui calori di combustione di alcuni derivati del bifenil,
Gazz. Chim. Ital., 1935, 65, 19-28. [all data]
Mayer and Freitak, 1921
Mayer, F.; Freitak, K.,
Chem. Ber., 1921, 54, 347. [all data]
Perrier, 1892
Perrier, G.,
Bull. Soc. Chim. Fr., 1892, 7, 180. [all data]
Stolle, 1888
Stolle, E.,
Chem. Ber., 1888, 21, 1096. [all data]
Castro, Andrews, et al., 1958
Castro, C.E.; Andrews, L.J.; Keefer, R.M.,
Molecular Complexes of Hindered Biphenyl Derivatives,
J. Am. Chem. Soc., 1958, 80, 2322-6. [all data]
Johnson, 1957
Johnson, E.A.,
J. Chem. Soc., 1957, 1957, 4155. [all data]
Schultz, Rohde, et al., 1907
Schultz, G.; Rohde, G.; Vicari, F.,
Justus Liebigs Ann. Chem., 1907, 352, 111. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Pribilová and Pouchlý, 1974
Pribilová, J.; Pouchlý, J.,
Vapour pressure of some low-volatile hydrocarbons determined by the effusion method,
Collect. Czech. Chem. Commun., 1974, 39, 5, 1118-1124, https://doi.org/10.1135/cccc19741118
. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
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]
Maier and Turner, 1972
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part I. Biphenyls,
Faraday Discuss. Chem. Soc., 1972, 54, 149. [all data]
Zhang, Chen, et al., 1997
Zhang, M.; Chen, B.; Shen, S.; Chen, S.,
Compositional studies of high-temperature coal tar by g.c.-FT-i.r. analysis of middle oil fractions,
Fuel, 1997, 76, 5, 415-423, https://doi.org/10.1016/S0016-2361(97)85518-4
. [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
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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,
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Beernaert, 1979
Beernaert, H.,
Gas Chromatographic Analysis of Polyclylic Aromatic Hydrocarbons,
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. [all data]
Chung, Yung, et al., 2002
Chung, H.-Y.; Yung, I.K.S.; Ma, W.C.J.; Kim, J.-S.,
Analysis of volatile components in frozen and dried scallops (Patinopecten yessoensis) by gas chromatography/mass spectrometry,
Food Res. Int., 2002, 35, 1, 43-53, https://doi.org/10.1016/S0963-9969(01)00107-7
. [all data]
Chung, Yung, et al., 2001
Chung, H.Y.; Yung, I.K.S.; Kim, J.-S.,
Comparison of volatile components in dried scallops (Chlamys farreri and Patinopecten yessoensis) prepared by boiling and steaming methods,
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Chung, 1999
Chung, H.Y.,
Volatile components in crabmeats of Charybdis feriatus,
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Ferrand, 1962
Ferrand, R.,
Gas phase chromatography using retention indices for the analysis of tars and their hydrogenation products,
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Radulovic, Blagojevic, et al., 2010
Radulovic, N.; Blagojevic, P.; Palic, R.,
Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae),
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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
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Tong, Centen, et al., 1985
Tong, H.Y.; Centen, J.D.; Karasek, F.W.; Jellum, E.; Helland, P.,
Identification of Trace Organic Compounds in Dimethyl Sulphoxide Solution Using High-Performance Liquid Chromatography and Gas Chromatography-Mass Spectrometry,
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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,
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Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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