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 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
Δ_fH°_gas	398.1 ± 6.9	kJ/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
Δ_fH°_gas	393. ± 6.3	kJ/mol	Cm	Kana'an, 1972	ALS
Quantity	Value	Units	Method	Reference	Comment
S°_gas	639.	J/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/molK [85MAR/LOE, Dorofeeva O.V., 1997]). Value obtained from calorimetric data (660.6 J/molK [85MAR/LOE]) authors do not regard as reliable.; GT

Condensed phase thermochemistry data

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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
Δ_fH°_solid	247.2 ± 4.1	kJ/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
Δ_fH°_solid	292.	kJ/mol	Ccb	Schmidlin, 1906	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-12943.2 ± 2.5	kJ/mol	Ccb	Coops, Mulder, et al., 1947	Reanalyzed by Cox and Pilcher, 1970, Original value = -12933.4 ± 2.0 kJ/mol; See Coops, Mulder, et al., 1946; Corresponding Δ_fHº_solid = 247.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-13000.	kJ/mol	Ccb	Wieland, Heymann, et al., 1934	Corresponding Δ_fHº_solid = 300. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-12988.	kJ/mol	Ccb	Schmidlin, 1906	Corresponding Δ_fHº_solid = 292. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
368.2	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 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
T_fus	554.6	K	N/A	Kana'an, 1972, 2	Uncertainty assigned by TRC = 1. K; TRC
T_fus	556.15	K	N/A	Smith and Andrews, 1931, 2	Uncertainty assigned by TRC = 1.5 K; TRC
T_fus	553.15	K	N/A	Gomberg and Kamm, 1917	Uncertainty assigned by TRC = 3. K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	150.9 ± 5.6	kJ/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
Δ_subH°	140.0 ± 1.3	kJ/mol	GS	Verevkin, 1999	Based on data from 363. to 388. K.; AC
Δ_subH°	151. ± 4.2	kJ/mol	V	Kana'an, 1972	ALS
Δ_subH°	151. ± 4.	kJ/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

Δ_subH (kJ/mol)	Temperature (K)	Method	Reference	Comment
135.4 ± 1.3	376.	GS	Verevkin, 1999	Based on data from 363. to 383. K.; AC
143.3	419.	N/A	Stephenson and Malanowski, 1987	Based on data from 404. to 466. K.; AC

Enthalpy of fusion

Δ_fusH (kJ/mol)	Temperature (K)	Method	Reference	Comment
48.28	554.2	DSC	Verevkin, 1999	AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Notes

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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References

Symbols used in this document:

C_p,solid	Constant pressure heat capacity of solid
S°_gas	Entropy of gas at standard conditions
T_fus	Fusion (melting) point
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_subH	Enthalpy of sublimation
Δ_subH°	Enthalpy of sublimation at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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