p-Terphenyl
- Formula: C18H14
- Molecular weight: 230.3038
- IUPAC Standard InChIKey: XJKSTNDFUHDPQJ-UHFFFAOYSA-N
- CAS Registry Number: 92-94-4
- 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. - Isotopologues:
- Other names: 1,1':4',1''-Terphenyl; p-Diphenylbenzene; p-Triphenyl; Santowax P; 1,1'-Biphenyl, 4-phenyl-; 1,4-Diphenylbenzene; 4-Phenylbiphenyl; 4-Phenyldiphenyl; Biphenyl, 4-phenyl-; NSC 6810; PT; PTP
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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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 284.4 ± 3.8 | kJ/mol | Review | Roux, Temprado, et al., 2008 | There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB |
ΔfH°gas | 279. ± 6.3 | kJ/mol | Ccb | Balepin, Lebedev, et al., 1977 | ALS |
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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 158.8 ± 3.4 | kJ/mol | Review | Roux, Temprado, et al., 2008 | There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB |
ΔfH°solid | 163. ± 4.6 | kJ/mol | Ccb | Balepin, Lebedev, et al., 1977 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -9246.6 ± 4.6 | kJ/mol | Ccb | Balepin, Lebedev, et al., 1977 | Corresponding ΔfHºsolid = 163. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 285.23 | J/mol*K | N/A | Saito, Atake, et al., 1988 | crystaline, I phase; DH |
S°solid,1 bar | 285.62 | J/mol*K | N/A | Chang, 1983 | DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
278.12 | 298.15 | Saito, Atake, et al., 1988 | crystaline, I phase; T = 5 to 300 K.; DH |
278.68 | 298.15 | Chang, 1983 | T = 4 to 580 K. Cp = 35.12 + 0.58825T + 0.0010062T2 - 8.042x10-7T3 from 80 to 300 K.; DH |
260. | 300. | Wasicki, Radomska, et al., 1982 | T = 180 to 500 K. Data given graphically. Value estimated from graph.; DH |
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
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 662.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 493.1 | K | N/A | Wasicki, Radomska, et al., 1982, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 487.5 | K | N/A | Sangster and Irvine, 1956 | Uncertainty assigned by TRC = 5. K; TRC |
Tfus | 488.1 | K | N/A | Sangster and Irvine, 1956 | Uncertainty assigned by TRC = 4. K; TRC |
Tfus | 486. | K | N/A | Mikhailov and Aronovich, 1955 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 480. | K | N/A | Ipatieff, Germain, et al., 1953 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 487.0 | K | N/A | Chang, 1983, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 908. ± 10. | K | N/A | Tsonopoulos and Ambrose, 1995 | |
Tc | 908. | K | N/A | Reiter, 1963 | Uncertainty assigned by TRC = 10. K; TRC |
Tc | 925.9 | K | N/A | Mandel and Ewbank, 1960 | Uncertainty assigned by TRC = 16.7 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 30. ± 6. | bar | N/A | Tsonopoulos and Ambrose, 1995 | |
Pc | 29.90 | bar | N/A | Reiter, 1963 | Uncertainty assigned by TRC = 6.0795 bar; TRC |
Pc | 33.30 | bar | N/A | Mandel and Ewbank, 1960 | Uncertainty assigned by TRC = 3.447 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.729 | l/mol | N/A | Tsonopoulos and Ambrose, 1995 | |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 1.4 ± 0.6 | mol/l | N/A | Tsonopoulos and Ambrose, 1995 | |
ρc | 1.37 | mol/l | N/A | Reiter, 1963 | Uncertainty assigned by TRC = 0.087 mol/l; TRC |
ρc | 1.31 | mol/l | N/A | Mandel and Ewbank, 1960 | Uncertainty assigned by TRC = 0.13 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 101.7 | kJ/mol | CGC | Zhao, Unhannanant, et al., 2008 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 119. ± 9. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
79.2 | 398. | GC | Lei, Chankalal, et al., 2002 | Based on data from 323. to 473. K.; AC |
79.2 | 514. | A | Stephenson and Malanowski, 1987 | Based on data from 499. to 700. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
116.2 ± 2.4 | 368. | T | Verevkin, 1997 | Based on data from 353. to 383. K.; AC |
118.4 | 397. | ME | Wakayama and Inokuchi, 1967 | AC |
120.6 | 363. | N/A | Hoyer and Peperle, 1958 | Based on data from 333. to 393. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
35.300 | 487.0 | N/A | Chang, 1983 | DH |
35.500 | 486.3 | N/A | Smith, 1979 | DH |
41.600 | 493.1 | N/A | Wasicki, Radomska, et al., 1982 | DH |
35.3 | 482.4 | DSC | Verevkin, 1997 | AC |
35.5 | 486.3 | N/A | Saito, Atake, et al., 1988 | See also Chang, 1983, 2 and Acree, 1991.; AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
72.5 | 487.0 | Chang, 1983 | DH |
73.0 | 486.3 | Smith, 1979 | DH |
84.4 | 493.1 | Wasicki, Radomska, et al., 1982 | DH |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
193.55 | crystaline, II | crystaline, I | Chang, 1983 | Lambda transition.; DH |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.304 | 193.5 | crystaline, II | crystaline, I | Saito, Atake, et al., 1988 | DH |
0.095 | 193.3 | crystaline, II | crystaline, I | Cailleau and Dworkin, 1979 | Obtained T = 191.0 K, S = 0.45 J/mol, from DSC data.; DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.63 | 193.5 | crystaline, II, Lambda | crystaline, I, type transition | Saito, Atake, et al., 1988 | DH |
0.49 | 193.3 | crystaline, II | crystaline, I | Cailleau and Dworkin, 1979 | Obtained; DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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:
L - Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.80 ± 0.03 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.83 | PE | Hino, Seki, et al., 1975 | LLK |
7.78 ± 0.01 | PE | Dewar and Goodman, 1972 | LLK |
8.29 | CTS | Slifkin and Allison, 1967 | RDSH |
8.78 ± 0.05 | EI | Gallegos, 1967 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118487 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Roux, Temprado, et al., 2008
Roux, M.V.; Temprado, M.; Chickos, J.S.; Nagano, Y.,
Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons,
J. Phys. Chem. Ref. Data, 2008, 37, 4, 1855-1996. [all data]
Balepin, Lebedev, et al., 1977
Balepin, A.A.; Lebedev, V.P.; Miroshnichenko, E.A.; Koldobskii, G.I.; Ostovskii, V.A.; Larionov, B.P.; Gidaspov, B.V.; Lebedev, Yu.A.,
Energy effects in polyphenylenes and phenyltetrazoles,
Svoistva Veshchestv Str. Mol., 1977, 93-98. [all data]
Saito, Atake, et al., 1988
Saito, K.; Atake, T.; Chihara, H.,
Thermodynamic studies on order-disorder phase transitions of p-terphenyl and p-terphenyl-d14,
Bull. Chem. Soc. Japan, 1988, 61, 2327-2336. [all data]
Chang, 1983
Chang, S.S.,
Heat capacity and thermodynamic properties of p-terphenyl: study of order-disorder transition by automated high-resolution adiabatic calorimetry,
J. Chem. Phys., 1983, 79, 6229-6236. [all data]
Wasicki, Radomska, et al., 1982
Wasicki, J.; Radomska, M.; Radomski, R.,
Heat capacities of diphenyl, p-terphenyl and p-quaterphenyl from 180 K to their melting points,
J. Therm. Anal., 1982, 25, 509-514. [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]
Wasicki, Radomska, et al., 1982, 2
Wasicki, J.; Radomska, M.; Radomski, R.,
Heat capacities of diphenyl, p-terphenyl and p-quaterphenyl from 180 K to their melting points,
J. Therm. Anal., 1982, 25, 509. [all data]
Sangster and Irvine, 1956
Sangster, R.C.; Irvine, J.W.,
Study of Organic Scintillators,
J. Chem. Phys., 1956, 24, 670. [all data]
Mikhailov and Aronovich, 1955
Mikhailov, B.M.; Aronovich, P.M.,
Preparation of p-terphenyl,
Izv. Akad. Nauk SSSR, 1955, 1955, 945. [all data]
Ipatieff, Germain, et al., 1953
Ipatieff, V.N.; Germain, J.E.; Pines, H.,
The Structure of Di-(methylcyclohexyl)-benzene from Cycloalkylation of 4-Methylcyclohexane with Benzene in the Presence of Hydrogen Fluoride,
J. Am. Chem. Soc., 1953, 75, 6056. [all data]
Chang, 1983, 2
Chang, Shu-Sing,
Heat capacity and thermodynamic properties of p-terphenyl: Study of order--disorder transition by automated high-resolution adiabatic calorimetry,
J. Chem. Phys., 1983, 79, 12, 6229, https://doi.org/10.1063/1.445727
. [all data]
Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D.,
Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons,
J. Chem. Eng. Data, 1995, 40, 547-558. [all data]
Reiter, 1963
Reiter, R.W.,
, NASA Doc. N63-19495 1963 1963, 1963. [all data]
Mandel and Ewbank, 1960
Mandel, H.; Ewbank, N.,
, Atomics International NAA-S-R-5129 1960, 1960. [all data]
Zhao, Unhannanant, et al., 2008
Zhao, Hui; Unhannanant, Patamaporn; Hanshaw, William; Chickos, James S.,
Enthalpies of Vaporization and Vapor Pressures of Some Deuterated Hydrocarbons. Liquid-Vapor Pressure Isotope Effects,
J. Chem. Eng. Data, 2008, 53, 7, 1545-1556, https://doi.org/10.1021/je800091s
. [all data]
Lei, Chankalal, et al., 2002
Lei, Ying Duan; Chankalal, Raymond; Chan, Anita; Wania, Frank,
Supercooled Liquid Vapor Pressures of the Polycyclic Aromatic Hydrocarbons,
J. Chem. Eng. Data, 2002, 47, 4, 801-806, https://doi.org/10.1021/je0155148
. [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]
Verevkin, 1997
Verevkin, S.P.,
Thermochemistry of substituted benzenes. Experimental standard molar enthalpies of formation of o-, m-, and p-terphenyls and 1,3,5-triphenylbenzene,
J. Chem. Thermodyn., 1997, 29, 1495-1501. [all data]
Wakayama and Inokuchi, 1967
Wakayama, Nobuko; Inokuchi, Hiroo,
Heats of Sublimation of Polycyclic Aromatic Hydrocarbons and Their Molecular Packings,
Bull. Chem. Soc. Jpn., 1967, 40, 10, 2267-2271, https://doi.org/10.1246/bcsj.40.2267
. [all data]
Hoyer and Peperle, 1958
Hoyer, H.; Peperle, W.,
Z. Elektrochem., 1958, 62, 61. [all data]
Smith, 1979
Smith, G.W.,
Phase behavior of some linear polyphenyls,
Mol. Cryst. Liq. Cryst., 1979, 49, 207-209. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Cailleau and Dworkin, 1979
Cailleau, H.; Dworkin, A.,
Calorimetric study of the phase transition of para-terphenyl,
Mol. Cryst. Liq. Cryst., 1979, 50, 217-222. [all data]
Hino, Seki, et al., 1975
Hino, S.; Seki, K.; Inokuchi, H.,
Photoelectron spectra of p-terphenyl in gaseous and solid states,
Chem. Phys. Lett., 1975, 36, 335. [all data]
Dewar and Goodman, 1972
Dewar, M.J.S.; Goodman, D.W.,
Photoelectron spectra of molecules. Part 5.--Polycyclic aromatic hydrocarbons,
J. Chem. Soc. Faraday Trans. 2, 1972, 68, 1784. [all data]
Slifkin and Allison, 1967
Slifkin, M.A.; Allison, A.C.,
Measurement of ionization potentials from contact charge transfer spectra,
Nature, 1967, 215, 949. [all data]
Gallegos, 1967
Gallegos, E.J.,
Mass spectrometry of some polyphenyls,
J. Phys. Chem., 1967, 71, 1647. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid IE (evaluated) Recommended ionization energy Pc Critical pressure S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Ttrs Temperature of phase transition Vc Critical volume ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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