1,1':3',1''-Terphenyl, 5'-phenyl-
- Formula: C24H18
- Molecular weight: 306.3997
- IUPAC Standard InChIKey: SXWIAEOZZQADEY-UHFFFAOYSA-N
- CAS Registry Number: 612-71-5
- 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: m-Terphenyl, 5'-phenyl-; Benzene, 1,3,5-triphenyl-; 1,1'-Biphenyl, 3,5-diphenyl-; 1,3,5-Triphenylbenzene; s-Triphenylbenzene; Triphenylbenzene; 5'-Phenyl-m-terphenyl; Symmetrical triphenylbenzene; 5'-Phenyl-1,1':3',1''-terphenyl; NSC 17358
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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: Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 371.8 ± 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. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change 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 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 | 222. ± 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 | 224.6 ± 5.4 | kJ/mol | Ccb | Richardson and Parks, 1939 | Reanalyzed by Cox and Pilcher, 1970, Original value = 221.4 kJ/mol; see Richardson, 1939; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -12241.3 ± 5.3 | kJ/mol | Ccb | Richardson and Parks, 1939 | Reanalyzed by Cox and Pilcher, 1970, Original value = -12236.1 kJ/mol; see Richardson, 1939; Corresponding ΔfHºsolid = 224.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 375.5 | J/mol*K | N/A | Lebedev, Bykova, et al., 1982 | DH |
S°solid,1 bar | 367.4 | J/mol*K | N/A | Parks, Todd, et al., 1936 | Extrapolation below 90 K, 114.64 J/mol*K.; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
361.0 | 298.15 | Lebedev, Bykova, et al., 1982 | T = 13.8 to 480 K.; DH |
358.32 | 298.1 | Parks, Todd, et al., 1936 | T = 90 to 300 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, 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 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 | 733.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 450.1 | K | N/A | Sangster and Irvine, 1956 | Uncertainty assigned by TRC = 4. K; TRC |
Tfus | 448. | K | N/A | Baxter and Hale, 1936 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 444. | K | N/A | Parks, Todd, et al., 1936, 2 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 446. | K | N/A | Adkins, Zartman, et al., 1931 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 446. | K | N/A | Lebedev, Bykova, et al., 1982, 2 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 133.4 ± 2.0 | kJ/mol | GCG | Hanshaw, Nutt, et al., 2008 | AC |
ΔvapH° | 140. | kJ/mol | CGC | Chickos, Hesse, et al., 1998 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 149. ± 6. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
77.5 | 515. | A | Stephenson and Malanowski, 1987 | Based on data from 500. to 735. K. See also Vohra, Kang, et al., 1962.; AC |
118. | 469. | A | Stephenson and Malanowski, 1987 | Based on data from 454. to 500. K. See also Malaspina, Bardi, et al., 1974.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
453.99 to 499.99 | 0.80427 | 684.343 | -316.422 | Malaspina, Bardi, et al., 1974 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
141.2 ± 0.7 | 418. | ME | Ribeiro da Silva, Monte, et al., 2006 | Based on data from 407. to 429. K.; AC |
145.6 ± 0.9 | 376. | T | Verevkin, 1997 | Based on data from 364. to 388. K.; AC |
142. | 425. | ME | Malaspina, Bardi, et al., 1974 | Based on data from 410. to 444. K. See also Stephenson and Malanowski, 1987.; AC |
142.2 | 422. | ME | Wakayama and Inokuchi, 1967 | Based on data from 384. to 400. K.; AC |
164.4 ± 4.2 | 363. | V | Hoyer and Peperle, 1958 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 141. kJ/mol; ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
33.400 | 446. | N/A | Lebedev, Bykova, et al., 1982 | DH |
32.6 | 445.2 | DSC | Verevkin, 1997 | AC |
33.4 | 446. | N/A | Lebedev, Bykova, et al., 1982, 2 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
75.1 | 446. | Lebedev, Bykova, et al., 1982 | DH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, 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]
Richardson and Parks, 1939
Richardson, J.W.; Parks, G.S.,
Thermal data on organic compounds. XIX. Modern combustion data for some non-volatile compounds containing carbon, hydrogen and oxygen,
J. Am. Chem. Soc., 1939, 61, 3543-3546. [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]
Richardson, 1939
Richardson, J.W.,
Precise determination of the heats of combustion of some representative organic compounds, Ph.D. Thesis for Standford University, 1939, 1-122. [all data]
Lebedev, Bykova, et al., 1982
Lebedev, B.V.; Bykova, T.A.; Smirnova, N.N.; Kulagina, T.G.,
Thermodynmics of phenylacetylene, its cyclotrimerization, and the resulting 1,3,5-triphenylbenzene at 0-480 K,
Zhur. Obshch. Khim., 1982, 52, 2630-2636. [all data]
Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Moore, W.A.,
Thermal data on organic compounds. XVI. Some heat capacity, entropy and free energy data for typical benzene derivatives and heterocyclic compounds,
J. Am. Chem. Soc., 1936, 58, 398-401. [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]
Sangster and Irvine, 1956
Sangster, R.C.; Irvine, J.W.,
Study of Organic Scintillators,
J. Chem. Phys., 1956, 24, 670. [all data]
Baxter and Hale, 1936
Baxter, G.P.; Hale, A.H.,
A Revision of the Atomic Weight of Carbon,
J. Am. Chem. Soc., 1936, 58, 510. [all data]
Parks, Todd, et al., 1936, 2
Parks, G.S.; Todd, S.S.; Shomate, C.H.,
Thermal data on organic compounds. XVII. Some heat capacity, entropy and free energy data for five higher olefins,
J. Am. Chem. Soc., 1936, 58, 2505. [all data]
Adkins, Zartman, et al., 1931
Adkins, H.; Zartman, W.H.; Cramer, H.,
The Hydrogention of Certain Branched Compounds Over Nickel,
J. Am. Chem. Soc., 1931, 53, 1425. [all data]
Lebedev, Bykova, et al., 1982, 2
Lebedev, B.V.; Bykova, T.A.; Smirnova, N.N.; Kulagina, T.G.,
Zh. Obshch. Khim., 1982, 52, 2630. [all data]
Hanshaw, Nutt, et al., 2008
Hanshaw, William; Nutt, Marjorie; Chickos, James S.,
Hypothetical Thermodynamic Properties. Subcooled Vaporization Enthalpies and Vapor Pressures of Polyaromatic Hydrocarbons,
J. Chem. Eng. Data, 2008, 53, 8, 1903-1913, https://doi.org/10.1021/je800300x
. [all data]
Chickos, Hesse, et al., 1998
Chickos, James; Hesse, Donald; Hosseini, Sarah; Nichols, Gary; Webb, Paul,
Sublimation enthalpies at 298.15K using correlation gas chromatography and differential scanning calorimetry measurements,
Thermochimica Acta, 1998, 313, 2, 101-110, https://doi.org/10.1016/S0040-6031(97)00432-2
. [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]
Vohra, Kang, et al., 1962
Vohra, S.P.; Kang, T.L.; Kobe, K.A.; McKetta, J.J.,
P-V-T Properties of Propyne.,
J. Chem. Eng. Data, 1962, 7, 1, 150-155, https://doi.org/10.1021/je60012a044
. [all data]
Malaspina, Bardi, et al., 1974
Malaspina, L.; Bardi, G.; Gigli, R.,
Simultaneous determination by knudsen-effusion microcalorimetric technique of the vapor pressure and enthalpy of vaporization of pyrene and 1,3,5-triphenylbenzene,
The Journal of Chemical Thermodynamics, 1974, 6, 11, 1053-1064, https://doi.org/10.1016/0021-9614(74)90067-6
. [all data]
Ribeiro da Silva, Monte, et al., 2006
Ribeiro da Silva, Manuel A.V.; Monte, Manuel J.S.; Santos, Luís M.N.B.F.,
The design, construction, and testing of a new Knudsen effusion apparatus,
The Journal of Chemical Thermodynamics, 2006, 38, 6, 778-787, https://doi.org/10.1016/j.jct.2005.08.013
. [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.,
Dampfdrunkmessungen an organischen substanzen und ihre sublimationswarmen,
Z. Electrochem., 1958, 62, 61-66. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.