3,3'-Dimethylbiphenyl
- Formula: C14H14
- Molecular weight: 182.2610
- 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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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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -1799.7 ± 1.8 | kcal/mol | Ccb | Brull, 1935 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1799.14 kcal/mol; Corresponding ΔfHºliquid = 4.78 kcal/mol (simple calculation by NIST; no Washburn corrections) |
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:
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° | 17.2 | kcal/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° | 17.2 | kcal/mol | ME | Pribilová and Pouchlý, 1974 | Based on data from 288. to 308. K.; AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
559.2 | 0.938 | Aldrich Chemical Company Inc., 1990 | BS |
423.2 | 0.024 | Weast and Grasselli, 1989 | BS |
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
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 |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-8383 |
NIST MS number | 229735 |
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
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Source | Woods, van Artsdale, et al., 1950 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 692 |
Instrument | Beckman spectrophotometer |
Melting point | 9 |
Boiling point | 280 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change 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.
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]
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]
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]
Woods, van Artsdale, et al., 1950
Woods, G.F.; van Artsdale, A.L.; Reed, F.T.,
Synthesis and ultraviolet absorption spectra of m-di-substituted benzenes,
J. Am. Chem. Soc., 1950, 72, 3221-3226. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions 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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