1,1'-Biphenyl, 4-methyl-
- Formula: C13H12
- Molecular weight: 168.2344
- IUPAC Standard InChI: InChI=1S/C13H12/c1-11-7-9-13(10-8-11)12-5-3-2-4-6-12/h2-10H,1H3
- IUPAC Standard InChIKey: ZZLCFHIKESPLTH-UHFFFAOYSA-N
- CAS Registry Number: 644-08-6
- 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: Biphenyl, 4-methyl-; p-Methylbiphenyl; p-Methyldiphenyl; 4-Methylbiphenyl; 4-Methyldiphenyl; 4-Phenyltoluene; 1-Methyl-4-phenylbenzene; FEMA 3186; 4-Methyl-1,1'-biphenyl; p-Phenyltoluene; (4-Methylphenyl)benzene; NSC 407669
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Condensed phase thermochemistry data
Go To: Top, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 13.9 ± 0.60 | kcal/mol | Ccb | Ribeiro da Silva, Matos, et al., 1997 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1646.4 ± 0.43 | kcal/mol | Ccb | Ribeiro da Silva, Matos, et al., 1997 | Corresponding ΔfHºsolid = 13.9 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -1645.8 ± 1.7 | kcal/mol | Ccb | Brull, 1935 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1645.43 kcal/mol; Corresponding ΔfHºsolid = 13.25 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 195.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 187.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.6 ± 0.1 | EI | Bohlmann, Koppel, et al., 1974 | LLK |
| 7.80 ± 0.02 | PE | Maier and Turner, 1972 | LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C7H7+ | 13.7 ± 0.3 | ? | EI | McLafferty and Winkler, 1974 | LLK |
| C13H11+ | 11.3 ± 0.1 | H | EI | Bohlmann, Koppel, et al., 1974 | LLK |
References
Go To: Top, Condensed phase thermochemistry 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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Bohlmann, Koppel, et al., 1974
Bohlmann, F.; Koppel, C.; Muller, B.; Schwarz, H.; Weyerstahl, P.,
Massenspektrometrische Untersuchung isomerer Kohlenwasserstoffe: Struktur und Bildungsenthalpie stabiler (C13H11+) Ionen,
Tetrahedron, 1974, 30, 1011. [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]
McLafferty and Winkler, 1974
McLafferty, F.W.; Winkler, J.,
Gaseous tropylium, benzyl, tolyl, and norbornadienyl cations,
J. Am. Chem. Soc., 1974, 96, 5182. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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