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
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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

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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	39.4 ± 0.53	kcal/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	38.79 ± 0.55	kcal/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	39.39 ± 0.38	kcal/mol	Ccb	Steele, Chirico, et al., 1995	ALS
Δ_fH°_gas	37.43	kcal/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	104.	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 (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	23.2 ± 0.53	kcal/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	23.2 ± 0.33	kcal/mol	Ccb	Steele, Chirico, et al., 1995	ALS
Δ_fH°_liquid	21.25	kcal/mol	Ccb	Parks and Mosley, 1950	see Parks, West, et al., 1946; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1655.6 ± 0.33	kcal/mol	Ccb	Steele, Chirico, et al., 1995	Corresponding Δ_fHº_liquid = 23.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1653.83 ± 0.32	kcal/mol	Ccb	Parks and Mosley, 1950	see Parks, West, et al., 1946; Corresponding Δ_fHº_liquid = 21.28 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	17.9 ± 0.53	kcal/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	27.3	kcal/mol	Ccb	Schmidlin, 1906	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-1595.	kcal/mol	Ccb	Serijan and Wise, 1951	Corresponding Δ_fHº_solid = -38. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1656.6	kcal/mol	Ccb	Wise, Serijan, et al., 1951	Corresponding Δ_fHº_solid = 24.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1656.20 ± 0.20	kcal/mol	Ccb	Coops, Mulder, et al., 1946	Reanalyzed by Cox and Pilcher, 1970, Original value = -1655.6 ± 0.2 kcal/mol; Corresponding Δ_fHº_solid = 23.65 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1659.9	kcal/mol	Ccb	Schmidlin, 1906	Corresponding Δ_fHº_solid = 27.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	57.19	cal/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 (cal/mol*K)	Temperature (K)	Reference	Comment
63.60	303.	Duff and Everett, 1956	T = 303 to 353 K.; DH
66.90	300.	Kurbatov, 1950	T = 29 to 254°C.; DH
55.81	298.5	Smith and Andrews, 1931	T = 102 to 322 K. Value is unsmoothed experimental datum.; DH
53.49	282.5	Huffman, Parks, et al., 1930	T = 89 to 312 K. Value is unsmoothed experimental datum.; DH

Reaction thermochemistry data

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Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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Individual Reactions

C₁₃H₁₁^- + = Diphenylmethane

By formula: C₁₃H₁₁^- + H⁺ = C₁₃H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	363.6 ± 2.1	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Δ_rH°	361.3 ± 2.3	kcal/mol	G+TS	Cumming and Kebarle, 1978	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	358.2 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Δ_rG°	355.9 ± 2.0	kcal/mol	IMRE	Cumming and Kebarle, 1978	gas phase; B

+ Diphenylmethane = ( • )

By formula: Cl^- + C₁₃H₁₂ = (Cl^- • C₁₃H₁₂)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	7.40	kcal/mol	TDEq	French, Ikuta, et al., 1982	gas phase; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
7.4	300.	PHPMS	French, Ikuta, et al., 1982	gas phase; M

References

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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]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Notes

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Symbols used in this document:

C_p,solid	Constant pressure heat capacity of solid
S°_gas	Entropy of gas at standard conditions
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
T	Temperature
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_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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