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
- IUPAC Standard InChIKey: RZTDESRVPFKCBH-UHFFFAOYSA-N
- 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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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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 111.3 ± 3.6 | kJ/mol | Ccb | Ribeiro da Silva, Matos, et al., 1997 |
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 |
|---|---|---|---|---|---|
| ΔfH°solid | 16.2 ± 2.9 | kJ/mol | Ccb | Ribeiro da Silva, Matos, et al., 1997 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -7526.1 ± 2.3 | kJ/mol | Ccb | Ribeiro da Silva, Matos, et al., 1997 | Corresponding ΔfHºsolid = 16.2 kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -7524.1 ± 7.5 | kJ/mol | Ccb | Brull, 1935 | Reanalyzed by Cox and Pilcher, 1970, Original value = -7521.74 kJ/mol; Corresponding ΔfHºsolid = 14.1 kJ/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:
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.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 568.2 | K | N/A | Weast and Grasselli, 1989 | BS |
| Tboil | 562. | K | N/A | Blades, Blades, et al., 1954 | Uncertainty assigned by TRC = 4. K; TRC |
| Tboil | 568. | K | N/A | Ullmann, 1904 | Uncertainty assigned by TRC = 4. K; TRC |
| Tboil | 569. | K | N/A | Schultz, 1881 | Uncertainty assigned by TRC = 4. K; TRC |
| Tboil | 559. | K | N/A | Carnelley, 1877 | Uncertainty assigned by TRC = 5. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 394. ± 3. | K | AVG | N/A | Average of 34 out of 35 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 95.1 ± 2.0 | kJ/mol | C | Ribeiro da Silva, Matos, et al., 1997 | ALS |
| ΔsubH° | 95.1 ± 2.0 | kJ/mol | C | Ribeiro da Silva, Matos, et al., 1997, 2 | AC |
| ΔsubH° | 95.1 | kJ/mol | N/A | N/A | DRB |
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 |
|---|---|---|---|
| 8.50 | EI | Loudon and Mazengo, 1974 | LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C13H11+ | 12.65 | CH3 | EI | Loudon and Mazengo, 1974 | LLK |
| C14H13+ | 12.85 | H | EI | Loudon and Mazengo, 1974 | LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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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