Diphenylmethane

Formula: C₁₃H₁₂
Molecular weight: 168.2344
IUPAC Standard InChI: InChI=1S/C13H12/c1-3-7-12(8-4-1)11-13-9-5-2-6-10-13/h1-10H,11H2
IUPAC Standard InChIKey: CZZYITDELCSZES-UHFFFAOYSA-N
CAS Registry Number: 101-81-5
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: Benzene, 1,1'-methylenebis-; Methane, diphenyl-; Benzene, (phenylmethyl)-; Benzylbenzene; Ditan; Ditane; Benzene, benzyl-; Toluene, α-phenyl-; 1,1'-Dimethylenebis(benzene); NSC 4708
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Gas phase thermochemistry data

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

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	165. ± 2.2	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
Δ_fH°_gas	162.3 ± 2.3	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
Δ_fH°_gas	164.8 ± 1.6	kJ/mol	Ccb	Steele, Chirico, et al., 1995	ALS
Δ_fH°_gas	156.6	kJ/mol	N/A	Parks and Mosley, 1950	Value computed using Δ_fH_liquid° value of 88.9 kj/mol from Parks and Mosley, 1950 and Δ_vapH° value of 67.7 kj/mol from Steele, Chirico, et al., 1995.; DRB
Quantity	Value	Units	Method	Reference	Comment
S°_gas	436.	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 (440-451 J/molK [85MAR/LOE, Dorofeeva O.V., 1997]). Value obtained from calorimetric data (508.5 J/molK [85MAR/LOE]) authors do not regard as reliable. Results of statistical thermodynamics calculation [ Puranik P.G., 1962] are likely to be erroneous (S(300 K)=319 J/mol*K).; 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°_liquid	97.1 ± 2.2	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
Δ_fH°_liquid	97.1 ± 1.4	kJ/mol	Ccb	Steele, Chirico, et al., 1995	ALS
Δ_fH°_liquid	88.91	kJ/mol	Ccb	Parks and Mosley, 1950	see Parks, West, et al., 1946; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-6927.2 ± 1.4	kJ/mol	Ccb	Steele, Chirico, et al., 1995	Corresponding Δ_fHº_liquid = 96.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-6919.6 ± 1.3	kJ/mol	Ccb	Parks and Mosley, 1950	see Parks, West, et al., 1946; Corresponding Δ_fHº_liquid = 89.04 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	75.1 ± 2.2	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
Δ_fH°_solid	114.	kJ/mol	Ccb	Schmidlin, 1906	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-6673.	kJ/mol	Ccb	Serijan and Wise, 1951	Corresponding Δ_fHº_solid = -160. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-6931.2	kJ/mol	Ccb	Wise, Serijan, et al., 1951	Corresponding Δ_fHº_solid = 100. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-6929.54 ± 0.84	kJ/mol	Ccb	Coops, Mulder, et al., 1946	Reanalyzed by Cox and Pilcher, 1970, Original value = -6927.0 ± 0.8 kJ/mol; Corresponding Δ_fHº_solid = 98.95 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-6945.0	kJ/mol	Ccb	Schmidlin, 1906	Corresponding Δ_fHº_solid = 114. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	239.3	J/mol*K	N/A	Huffman, Parks, et al., 1930	Extrapolation below 90 K, 77.86 J/mol*K.; DH

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
266.1	303.	Duff and Everett, 1956	T = 303 to 353 K.; DH
279.9	300.	Kurbatov, 1950	T = 29 to 254°C.; DH
233.5	298.5	Smith and Andrews, 1931	T = 102 to 322 K. Value is unsmoothed experimental datum.; DH
223.8	282.5	Huffman, Parks, et al., 1930	T = 89 to 312 K. Value is unsmoothed experimental datum.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity	Value	Units	Method	Reference	Comment
T_boil	535. ± 4.	K	AVG	N/A	Average of 51 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	299. ± 2.	K	AVG	N/A	Average of 83 out of 85 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_c	780. ± 60.	K	AVG	N/A	Average of 7 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
P_c	27. ± 3.	bar	N/A	Tsonopoulos and Ambrose, 1995
P_c	27.10	bar	N/A	Wieczorek and Kobayashi, 1980	Uncertainty assigned by TRC = 3.00 bar; TRC
P_c	59.7817	bar	N/A	Glaser and Ruland, 1957	Uncertainty assigned by TRC = 3.0398 bar; TRC
P_c	28.5736	bar	N/A	Guye and Mallet, 1902	Uncertainty assigned by TRC = 1.0132 bar; TRC
P_c	28.5736	bar	N/A	Guye and Mallet, 1902	Uncertainty assigned by TRC = 1.0132 bar; TRC
Quantity	Value	Units	Method	Reference	Comment
V_c	0.563	l/mol	N/A	Tsonopoulos and Ambrose, 1995
Quantity	Value	Units	Method	Reference	Comment
ρ_c	1.8 ± 0.3	mol/l	N/A	Tsonopoulos and Ambrose, 1995
ρ_c	1.780	mol/l	N/A	Stephenson, 1992	Uncertainty assigned by TRC = 0.12 mol/l; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	65. ± 10.	kJ/mol	AVG	N/A	Average of 10 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	87.2 ± 0.7	kJ/mol	Review	Roux, Temprado, et al., 2008	There are sufficient high-quality literature values to make a good evaluation with a high degree of confidence. In general, the evaluated uncertainty limits are on the order of (0.5 to 2.5) kJ/mol.; DRB
Δ_subH°	87.6 ± 0.8	kJ/mol	N/A	Verevkin, 1999	AC

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
64.1 ± 0.1	340.	IP,EB	Chirico and Steele, 2005	Based on data from 330. to 588. K.; AC
61.0 ± 0.1	380.	IP,EB	Chirico and Steele, 2005	Based on data from 330. to 588. K.; AC
57.9 ± 0.1	420.	IP,EB	Chirico and Steele, 2005	Based on data from 330. to 588. K.; AC
55.0 ± 0.1	460.	IP,EB	Chirico and Steele, 2005	Based on data from 330. to 588. K.; AC
52.0 ± 0.2	500.	IP,EB	Chirico and Steele, 2005	Based on data from 330. to 588. K.; AC
48.9 ± 0.3	540.	IP,EB	Chirico and Steele, 2005	Based on data from 330. to 588. K.; AC
66.4 ± 0.5	323.	GS	Verevkin, 1999	Based on data from 303. to 343. K.; AC
61.8	368.	N/A	Sohda, Okazaki, et al., 1990	Based on data from 353. to 433. K.; AC
63.7	363.	N/A	Sasse, N'guimbi, et al., 1989	Based on data from 303. to 402. K.; AC
72.2	310.	A	Stephenson and Malanowski, 1987	Based on data from 295. to 383. K.; AC
56.7	438.	A	Stephenson and Malanowski, 1987	Based on data from 423. to 583. K.; AC
55.8	445.	N/A	Wieczorek and Kobayashi, 1981	AC
49.0	535.	N/A	Wieczorek and Kobayashi, 1981	AC
54.2	505.	N/A	Crafts, 1915	Based on data from 490. to 555. K. See also Boublik, Fried, et al., 1984.; AC

Enthalpy of sublimation

Δ_subH (kJ/mol)	Temperature (K)	Method	Reference	Comment
88.5 ± 0.8	284.	GS	Verevkin, 1999	Based on data from 273. to 295. K.; AC
71.5	286.	EM	Sasse, N'guimbi, et al., 1989	Based on data from 273. to 298. K.; AC
83.3 ± 3.3	286.	HSA	Chickos, Annunziata, et al., 1986	Based on data from 276. to 295. K.; AC
82.47 ± 0.63	299.8	V	Aihara, 1959	crystal phase; ALS
64.0	278. to 299.	N/A	Bloink, Pausacker, et al., 1951	See also Jones, 1960.; AC
72.0 ± 0.8	297.	N/A	Wolf and Weghofer, 1938	AC
72.0 ± 0.8	297.	V	Wolf and Weghofer, 1938, 2	ALS

Enthalpy of fusion

Δ_fusH (kJ/mol)	Temperature (K)	Method	Reference	Comment
19.01	298.4	N/A	Chirico and Steele, 2005	AC
18.58	298.3	AC	Domalski and Hearing, 1996	AC
18.569	298.3	N/A	Huffman, Parks, et al., 1930	DH
19.050	299.4	N/A	Eykman, 1889	DH

Entropy of fusion

Δ_fusS (J/mol*K)	Temperature (K)	Reference	Comment
62.34	298.3	Domalski and Hearing, 1996	CAL
62.25	298.3	Huffman, Parks, et al., 1930	DH

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]

Steele, Chirico, et al., 1995
Steele, W.V.; Chirico, R.D.; Smith, N.K., The standard enthalpies of formation of 2-methylbiphenyl and diphenylmethane, J. Chem. Thermodyn., 1995, 27, 671-678. [all data]

Parks and Mosley, 1950
Parks, G.S.; Mosley, J.R., Redetermination of the heat of combustion of diphenylmethane, J. Am. Chem. Soc., 1950, 72, 1850. [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]

Puranik P.G., 1962
Puranik P.G., Vibrational spectra, potential constants, and thermodynamic properties of diphenylmethane, Proc. Indian Acad. Sci., 1962, A56, 233-238. [all data]

Parks, West, et al., 1946
Parks, G.S.; West, T.J.; Naylor, B.F.; Fujii, P.S.; McClaine, L.A., Thermal data on organic compounds. XXIII. Modern combustion data for fourteen hydrocarbons and five polyhydroxy alcohols, J. Am. Chem. Soc., 1946, 68, 2524-2527. [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]

Serijan and Wise, 1951
Serijan, K.T.; Wise, P.H., Dicyclic hydrocarbons. III. Diphenyl- and dicyclohexylalkanes through C₁₅, J. Am. Chem. Soc., 1951, 73, 4766-4769. [all data]

Wise, Serijan, et al., 1951
Wise, C.H.; Serijan, K.T.; Goodman, I.A., NACA Technical Report 1003, NACA Technical Report 1003, 1951, 1-10. [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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Huffman, Parks, et al., 1930
Huffman, H.M.; Parks, G.S.; Daniels, A.C., Thermal data on organic compounds. VII. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons, J. Am. Chem. Soc., 1930, 52, 1547-1558. [all data]

Duff and Everett, 1956
Duff, G.M.; Everett, D.H., The heat capacity of the system benzene + diphenylmethane, Trans. Faraday Soc., 1956, 52, 753-763. [all data]

Kurbatov, 1950
Kurbatov, V.Ya., Specific heats of liquids. III. Specific heat of hydrocarbons with several noncondensed rings, Zhur. Obshch. Khim., 1950, 20, 1139-1144. [all data]

Smith and Andrews, 1931
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, 3644-3660. [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]

Wieczorek and Kobayashi, 1980
Wieczorek, S.A.; Kobayashi, R., Vapor pressure measurements of diphenylmethane, thianaphthene, and bicyclohexyl at elevated temperatures, J. Chem. Eng. Data, 1980, 25, 302. [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [all data]

Guye and Mallet, 1902
Guye, P.A.; Mallet, E., Measurement of Critical Constants, Arch. Sci. Phys. Nat., 1902, 13, 274-296. [all data]

Stephenson, 1992
Stephenson, R.M., Mutual solubilities: water-ketones, water-ethers, and water-gasoline- alcohols, J. Chem. Eng. Data, 1992, 37, 80-95. [all data]

Verevkin, 1999
Verevkin, Sergey P., Thermochemical Properties of Diphenylalkanes, J. Chem. Eng. Data, 1999, 44, 2, 175-179, https://doi.org/10.1021/je980200e . [all data]

Chirico and Steele, 2005
Chirico, Robert D.; Steele, William V., Thermodynamic Properties of Diphenylmethane ^«8224», J. Chem. Eng. Data, 2005, 50, 3, 1052-1059, https://doi.org/10.1021/je050034s . [all data]

Sohda, Okazaki, et al., 1990
Sohda, M.; Okazaki, M.; Iwai, Y.; Arai, Y.; Sakoguchi, A.; Ueoka, R.; Kato, Y., Vapor pressures of cyclohexylbenzene and diphenylmethane, The Journal of Chemical Thermodynamics, 1990, 22, 6, 607-608, https://doi.org/10.1016/0021-9614(90)90152-G . [all data]

Sasse, N'guimbi, et al., 1989
Sasse, K.; N'guimbi, J.; Jose, J.; Merlin, J.C., Tension de vapeur d'hydrocarbures polyaromatiques dans le domaine 10-3--10 Torr, Thermochimica Acta, 1989, 146, 53-61, https://doi.org/10.1016/0040-6031(89)87075-3 . [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]

Wieczorek and Kobayashi, 1981
Wieczorek, Stefan A.; Kobayashi, Riki, Vapor-pressure measurements of 1-methylnaphthalene, 2-methylnaphthalene, and 9,10-dihydrophenanthrene at elevated temperatures, J. Chem. Eng. Data, 1981, 26, 1, 8-11, https://doi.org/10.1021/je00023a005 . [all data]

Crafts, 1915
Crafts, J.M., J. Chim. Phys. Phys.-Chim. Biol., 1915, 13, 105. [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Chickos, Annunziata, et al., 1986
Chickos, J.S.; Annunziata, R.; Ladon, L.H.; Hyman, A.S.; Liebman, J.F., Estimating heats of sublimation of hydrocarbons. A semiempirical approach, J. Org. Chem., 1986, 51, 4311-4314. [all data]

Aihara, 1959
Aihara, A., Estimation of the energy of hydrogen bonds formed in crystals. I. Sublimation pressures of some organic molecular crystals and the additivity of lattice energy, Bull. Chem. Soc. Jpn., 1959, 32, 1242. [all data]

Bloink, Pausacker, et al., 1951
Bloink, G.J.; Pausacker, K.H.; Jones, A.S.; Lee, W.A.; Peacocke, A.R.; Bright, Norman F.H.; Moffatt, J.S.; Wilkinson, J.H., Notes, J. Chem. Soc., 1951, 622, https://doi.org/10.1039/jr9510000622 . [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.Z., Z. Phys. Chem. Abt. B, 1938, 39, 194. [all data]

Wolf and Weghofer, 1938, 2
Wolf, K.L.; Weghofer, H., Uber sublimationswarmen, Z. Phys. Chem., 1938, 39, 194-208. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Eykman, 1889
Eykman, J.F., Zur kryoskopischen Molekulargewichtsbestimmung, Z. Physik. Chem., 1889, 4, 497-519. [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
P_c	Critical pressure
S°_gas	Entropy of gas at standard conditions
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
V_c	Critical volume
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_subH	Enthalpy of sublimation
Δ_subH°	Enthalpy of sublimation at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions
ρ_c	Critical density

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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