1,1'-Biphenyl, 4-methyl-
- Formula: C13H12
- Molecular weight: 168.2344
- 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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 138.2 ± 2.9 | 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 | 58.0 ± 2.5 | kJ/mol | Ccb | Ribeiro da Silva, Matos, et al., 1997 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -6888.6 ± 1.8 | kJ/mol | Ccb | Ribeiro da Silva, Matos, et al., 1997 | Corresponding ΔfHºsolid = 58.0 kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -6886.0 ± 7.1 | kJ/mol | Ccb | Brull, 1935 | Reanalyzed by Cox and Pilcher, 1970, Original value = -6884.48 kJ/mol; Corresponding ΔfHºsolid = 55.44 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 | 541. ± 9. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 321. ± 3. | K | AVG | N/A | Average of 17 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 80.2 ± 1.4 | kJ/mol | C | Ribeiro da Silva, Matos, et al., 1997 | ALS |
ΔsubH° | 80.2 ± 1.4 | kJ/mol | C | Ribeiro da Silva, Matos, et al., 1997, 2 | AC |
ΔsubH° | 80.2 | kJ/mol | N/A | N/A | DRB |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
408.2 | 0.020 | 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 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) | 817.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 785.4 | kJ/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, 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]
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]
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]
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, 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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