Mercury, diphenyl-

Formula: C₁₂H₁₀Hg
Molecular weight: 354.80
IUPAC Standard InChI: InChI=1S/2C6H5.Hg/c2*1-2-4-6-5-3-1;/h2*1-5H;
IUPAC Standard InChIKey: HWMTUNCVVYPZHZ-UHFFFAOYSA-N
CAS Registry Number: 587-85-9
Chemical structure:
This structure is also available as a 2d Mol file
Other names: Benzene, mercuriodi-; Diphenylmercury
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Gas phase thermochemistry data

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Data compiled by: José A. Martinho Simões

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	410. ± 80.	kJ/mol	AVG	N/A	Average of 7 values; Individual data points

Condensed phase thermochemistry data

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Data compiled as indicated in comments:
MS - José A. Martinho Simões
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	300. ± 80.	kJ/mol	AVG	N/A	Average of 7 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-6434.2 ± 7.9	kJ/mol	CC-SB	Carson and Wilmshurst, 1971	MS
Δ_cH°_solid	-6431.2 ± 7.5	kJ/mol	CC-SB	Fairbrother and Skinner, 1956	Please also see Cox and Pilcher, 1970.; MS
Δ_cH°_solid	-6549.2	kJ/mol	CC-SB	Berthelot, 1899	Please also see Berthelot, 1900.; MS

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
225.5	298.5	Smith and Andrews, 1931	T = 102 to 346 K. Value is unsmoothed experimental datum.; DH

Reaction thermochemistry data

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Data compiled as indicated in comments:
MS - José A. Martinho Simões
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

Mercury, diphenyl- (l) + Cl₂Hg (cr) = 2 (cr)

By formula: C₁₂H₁₀Hg (l) + Cl₂Hg (cr) = 2C₆H₅ClHg (cr)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-58.2 ± 2.1	kJ/mol	RSC	Chernick, Skinner, et al., 1956	Please also see Pedley and Rylance, 1977 and Cox and Pilcher, 1970.; MS

Mercury, diphenyl- (l) + (cr) = 2C₆H₅BrHg (cr)

By formula: C₁₂H₁₀Hg (l) + Br₂Hg (cr) = 2C₆H₅BrHg (cr)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-35.5 ± 1.2	kJ/mol	RSC	Hartley, Pritchard, et al., 1951	Please also see Pedley and Rylance, 1977 and Cox and Pilcher, 1970.; MS

Mercury, diphenyl- (l) + (cr) = 2 (cr)

By formula: C₁₂H₁₀Hg (l) + HgI₂ (cr) = 2C₆H₅HgI (cr)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-21.8 ± 0.8	kJ/mol	RSC	Hartley, Pritchard, et al., 1951	Please also see Pedley and Rylance, 1977 and Cox and Pilcher, 1970.; MS

2 + = Mercury, diphenyl- + 2

By formula: 2C₆H₅Br + Br₂Hg = C₁₂H₁₀Hg + 2Br₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	328.6 ± 3.3	kJ/mol	Cm	Chernick, Skinner, et al., 1956, 2	liquid phase; ALS

Gas phase ion energetics data

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Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.32	PE	Furlani, Piancastelli, et al., 1981	LLK
9.4 ± 0.2	EI	Glockling, Irwin, et al., 1976	LLK
8.30 ± 0.03	PI	Rodionov, Potapov, et al., 1973	LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₆H₅Hg⁺	11.5 ± 0.2	C₆H₅	EI	Glockling, Irwin, et al., 1976	LLK
Hg⁺	10.0 ± 0.2	?	EI	Glockling, Irwin, et al., 1976	LLK

References

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Carson and Wilmshurst, 1971
Carson, A.S.; Wilmshurst, B.R., J. Chem. Thermodyn., 1971, 3, 251. [all data]

Fairbrother and Skinner, 1956
Fairbrother, D.M.; Skinner, H.A., Trans. Faraday Soc., 1956, 52, 956. [all data]

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

Berthelot, 1899
Berthelot, M., Compt. Rend., 1899, 129, 918. [all data]

Berthelot, 1900
Berthelot, M., Ann. Chim. Phys., 1900, 20, 158. [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]

Chernick, Skinner, et al., 1956
Chernick, C.L.; Skinner, H.A.; Wadsö, I., Trans. Faraday Soc., 1956, 52, 1088. [all data]

Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brigton, 1977. [all data]

Hartley, Pritchard, et al., 1951
Hartley, K.; Pritchard, H.O.; Skinner, H.A., Thermochemistry of metallic alkyls. IV. Mercury diethyl and mercury diphenyl, Trans. Faraday Soc., 1951, 47, 254, https://doi.org/10.1039/tf9514700254 . [all data]

Chernick, Skinner, et al., 1956, 2
Chernick, C.L.; Skinner, H.A.; Wadso, I., Thermochemistry of metallic alkyls. Part 7.-The heat of formation of mercury diphenyl, and of mercury phenyl chloride, Trans. Faraday Soc., 1956, 52, 1088-1093. [all data]

Furlani, Piancastelli, et al., 1981
Furlani, C.; Piancastelli, M.N.; Cauletti, C.; Faticanti, F.; Ortaggi, G., He(I) and He(II) photoelectron spectra of some organomercury compounds with carbon π-systems, J. Electron Spectrosc. Relat. Phenom., 1981, 22, 309. [all data]

Glockling, Irwin, et al., 1976
Glockling, F.; Irwin, J.G.; Morrison, R.J.; Sweeney, J.J., A mass spectroscopic study of organomercurials and mercuric halides, Inorg. Chim. Acta, 1976, 19, 267. [all data]

Rodionov, Potapov, et al., 1973
Rodionov, A.N.; Potapov, V.K.; Rogozhin, K.L., Photoionization of certain aromatic heteroorganic compounds, High Energy Chem., 1973, 7, 249, In original 278. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,solid	Constant pressure heat capacity of solid
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_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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