Tetraphenylmethane
- Formula: C25H20
- Molecular weight: 320.4263
- IUPAC Standard InChI: InChI=1S/C25H20/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H
- IUPAC Standard InChIKey: PEQHIRFAKIASBK-UHFFFAOYSA-N
- CAS Registry Number: 630-76-2
- 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: Benzene, 1,1',1'',1'''-methanetetrayltetrakis-; Methane, tetraphenyl-
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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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 95.1 ± 1.6 | kcal/mol | Review | Roux, Temprado, et al., 2008 | There are insufficient literature values to properly evaluate the data and insufficient information to construct thermochemical cycles or estimate values for comparison, and one must rely solely upon reported uncertainities and the quality of the measurements. In general, the evaluated uncertainty limits are on the order of (3 to 9) kJ/mol.; DRB |
| ΔfH°gas | 93.9 ± 1.5 | kcal/mol | Cm | Kana'an, 1972 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 153. | cal/mol*K | N/A | Marcus Y., 1986 | This value calculated from published spectroscopic and structural data is in close agreement with estimations by a method of increments (654-673 J/mol*K [85MAR/LOE, Dorofeeva O.V., 1997]). Value obtained from calorimetric data (660.6 J/mol*K [85MAR/LOE]) authors do not regard as reliable.; GT |
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 | 59.08 ± 0.98 | kcal/mol | Review | Roux, Temprado, et al., 2008 | There are insufficient literature values to properly evaluate the data and insufficient information to construct thermochemical cycles or estimate values for comparison, and one must rely solely upon reported uncertainities and the quality of the measurements. In general, the evaluated uncertainty limits are on the order of (3 to 9) kJ/mol.; DRB |
| ΔfH°solid | 69.7 | kcal/mol | Ccb | Schmidlin, 1906 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3093.50 ± 0.60 | kcal/mol | Ccb | Coops, Mulder, et al., 1947 | Reanalyzed by Cox and Pilcher, 1970, Original value = -3091.15 ± 0.48 kcal/mol; See Coops, Mulder, et al., 1946; Corresponding ΔfHºsolid = 59.07 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -3106. | kcal/mol | Ccb | Wieland, Heymann, et al., 1934 | Corresponding ΔfHºsolid = 72. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -3104.1 | kcal/mol | Ccb | Schmidlin, 1906 | Corresponding ΔfHºsolid = 69.7 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 88.00 | 298.5 | Smith and Andrews, 1931 | T = 102 to 346 K. Value is unsmoothed experimental datum.; 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 554.6 | K | N/A | Kana'an, 1972, 2 | Uncertainty assigned by TRC = 1. K; TRC |
| Tfus | 556.15 | K | N/A | Smith and Andrews, 1931, 2 | Uncertainty assigned by TRC = 1.5 K; TRC |
| Tfus | 553.15 | K | N/A | Gomberg and Kamm, 1917 | Uncertainty assigned by TRC = 3. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 36.1 ± 1.3 | kcal/mol | Review | Roux, Temprado, et al., 2008 | There are insufficient literature values to properly evaluate the data and insufficient information to construct thermochemical cycles or estimate values for comparison, and one must rely solely upon reported uncertainities and the quality of the measurements. In general, the evaluated uncertainty limits are on the order of (3 to 9) kJ/mol.; DRB |
| ΔsubH° | 33.46 ± 0.31 | kcal/mol | GS | Verevkin, 1999 | Based on data from 363. to 388. K.; AC |
| ΔsubH° | 36.0 ± 1.0 | kcal/mol | V | Kana'an, 1972 | ALS |
| ΔsubH° | 36.0 ± 1. | kcal/mol | TE,ME | Kana'an, 1972, 2 | Based on data from 396. to 466. K. See also Pedley and Rylance, 1977.; AC |
Enthalpy of sublimation
| ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 32.36 ± 0.31 | 376. | GS | Verevkin, 1999 | Based on data from 363. to 383. K.; AC |
| 34.25 | 419. | N/A | Stephenson and Malanowski, 1987 | Based on data from 404. to 466. K.; AC |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 11.54 | 554.2 | DSC | Verevkin, 1999 | AC |
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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.0 | PE | Novak and Potts, 1984 | LBLHLM |
| 8.41 | PE | Novak and Potts, 1984 | Vertical value; LBLHLM |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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]
Kana'an, 1972
Kana'an, A.S.,
Sublimation pressures of tetraphenylmethane and associated bond energies,
J. Chem. Thermodyn., 1972, 4, 893. [all data]
Marcus Y., 1986
Marcus Y.,
Entropies of tetrahedral M-phenyl species,
J. Chem. Soc., Faraday Trans. 1, 1986, 82, 993-1006. [all data]
Dorofeeva O.V., 1997
Dorofeeva O.V.,
Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]
Schmidlin, 1906
Schmidlin, M.J.,
Recherches chimiques et thermochimiques sur la constitution des rosanilines,
Ann. Chim. Phys., 1906, 1, 195-256. [all data]
Coops, Mulder, et al., 1947
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J.,
Researches on heat of combustion IV. Technique for the determination of the heats of combustion of volatile liquids,
Recl. Trav. Chim. Pays-Bas, 1947, 66, 153-160. [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]
Coops, Mulder, et al., 1946
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J.,
The heats of combustion of a number of hydrocarbons,
Rec. Trav. Chim. Pays/Bas, 1946, 65, 128. [all data]
Wieland, Heymann, et al., 1934
Wieland, H.; Heymann, K.; Tsatsas, T.; Juchum, D.; Varvoglis, G.; Labriola, G.; Dobbelstein, O.; Boyd-Barrett, H.S.,
Uber das Auftreten freier Radikale bei chemischen Reaktionen. VIII,
Ann., 1934, 514, 145-181. [all data]
Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H.,
Thermal energy studies. II. Phenyl derivatives of metals,
J. Am. Chem. Soc., 1931, 53, 3661-3667. [all data]
Kana'an, 1972, 2
Kana'an, Adli S.,
Sublimation pressures of tetraphenylmethane and associated bond energies,
The Journal of Chemical Thermodynamics, 1972, 4, 6, 893-901, https://doi.org/10.1016/0021-9614(72)90011-0
. [all data]
Smith and Andrews, 1931, 2
Smith, R.H.; Andrews, D.H.,
Thermal Energy Studies I. Phenyl Derivatives of Methane, Ethane and Some Related Compounds,
J. Am. Chem. Soc., 1931, 53, 3644. [all data]
Gomberg and Kamm, 1917
Gomberg, M.; Kamm, O.,
J. Am. Chem. Soc., 1917, 39, 2009. [all data]
Verevkin, 1999
Verevkin, Sergey P.,
Thermochemical Properties of Triphenylalkanes and Tetraphenylmethane. Strain in Phenyl Substituted Alkanes,
J. Chem. Eng. Data, 1999, 44, 3, 557-562, https://doi.org/10.1021/je9802726
. [all data]
Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J.,
, Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [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]
Novak and Potts, 1984
Novak, I.; Potts, A.W.,
The UV gas-phase photoelectron spectra of Group IVB tetraphenyl derivatives,
J. Organomet. Chem., 1984, 262, 17. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°gas Entropy of gas at standard conditions 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 ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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