1,1'-Biphenyl, 2,2',3,3',4,4',5,5',6,6'-decafluoro-

Formula: C₁₂F₁₀
Molecular weight: 334.1124
IUPAC Standard InChI: InChI=1S/C12F10/c13-3-1(4(14)8(18)11(21)7(3)17)2-5(15)9(19)12(22)10(20)6(2)16
IUPAC Standard InChIKey: ONUFSRWQCKNVSL-UHFFFAOYSA-N
CAS Registry Number: 434-90-2
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: Biphenyl, decafluoro-; Decafluorobiphenyl; Perfluorobiphenyl; Perfluorodiphenyl; 1,1'-Biphenyl,decafluoro-; 2,2',3,3',4,4',5,5',6,6'-Decafluoro-1,1'-biphenyl
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Gas phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-1264.2 ± 5.8	kJ/mol	Ccb	Price and Sapiano, 1979	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -1263.2 ± 5.1 kJ/mol

Condensed phase thermochemistry data

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Data compiled as indicated in comments:
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_cH°_solid	-4404.1 ± 5.1	kJ/mol	Ccb	Price and Sapiano, 1979	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -4336.66 kJ/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	377.4	J/mol*K	N/A	Saito, Atake, et al., 1987	DH
S°_{solid,1 bar}	380.62	J/mol*K	N/A	Paukov and Rakhmenkulov, 1971	DH

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
317.4	298.15	Saito, Atake, et al., 1987	T = 3 to 300 K.; DH
323.4	300.7	Paukov and Rakhmenkulov, 1971	T = 13 to 350 K. Complete article deposited at VINITI, No. 2536-71, 2 January 1971.; DH

Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
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_boil	479.	K	N/A	PCR Inc., 1990	BS
T_boil	479.2	K	N/A	Weast and Grasselli, 1989	BS

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
49.9	468.	DSC	Back, Grzyll, et al., 1996	Based on data from 453. to 608. K.; AC

Enthalpy of sublimation

Δ_subH (kJ/mol)	Temperature (K)	Method	Reference	Comment
87.8	310.	A	Stephenson and Malanowski, 1987	Based on data from 297. to 323. K.; AC
85.3 ± 2.3	283.	V	Radchenko and Kitaigorodskii, 1974	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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

Electron affinity determinations

EA (eV)	Method	Reference	Comment
0.82 ± 0.11	IMRE	Dillow and Kebarle, 1989	ΔGea(423 K) = -20.5±1.0 kcal/mol , assumed entropy = 3.5 eu; B

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.40 ± 0.02	PE	Maier and Turner, 1972	LLK
10.0 ± 0.1	EI	Cotter, Soc. 1965	RDSH

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₁₁F₇⁺	17.2 ± 0.1	?	EI	Cotter, Soc. 1965	RDSH
C₁₂F₈⁺	18.4 ± 0.3	?	EI	Cotter, Soc. 1965	RDSH
C₁₂F₉⁺	16.7 ± 0.1	F	EI	Cotter, Soc. 1965	RDSH

References

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

Price and Sapiano, 1979
Price, S.J.W.; Sapiano, H.J., Determination of ΔH_f298(C₁₂F₁₀,g) from studies of the combustion of decafluorobiphenyl in oxygen and calculation of D(C₆F₅-C₆F₅), Can. J. Chem., 1979, 57, 1468-1470. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Saito, Atake, et al., 1987
Saito, K.; Atake, T.; Chihara, H., Perfluorobiphenyl and perchlorobiphenyl: heat capacities and intramolecular twisting vibrations, J. Chem. Thermodynam., 1987, 19, 9-18. [all data]

Paukov and Rakhmenkulov, 1971
Paukov, I.E.; Rakhmenkulov, F.S., Low-temperature heat capacity and standard thermodynamic functions of decafluorobiphenyl, Zhur. Fiz. Khim., 1971, 45, 1296-1297. [all data]

PCR Inc., 1990
PCR Inc., Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Back, Grzyll, et al., 1996
Back, Dwight D.; Grzyll, Lawrence R.; Corrigan, Mary, DSC enthalpy of vaporization measurements of high temperature two-phase working fluids, Thermochimica Acta, 1996, 272, 53-63, https://doi.org/10.1016/0040-6031(95)02615-0 . [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]

Radchenko and Kitaigorodskii, 1974
Radchenko, L.G.; Kitaigorodskii, A.I., The vapour pressures and heats of sublimation of naphthalene, biphenyl, octafluoronaphthalene, decafluorobiphenyl, acenaphthene and α-nitronaphthalene, Russ. J. Phys. Chem. (Engl. Transl.), 1974, 48, 1595. [all data]

Dillow and Kebarle, 1989
Dillow, G.W.; Kebarle, P., Substituent Effects on the Electron Affinities of Perfluorobenzenes C₆F₅X, J. Am. Chem. Soc., 1989, 111, 15, 5592, https://doi.org/10.1021/ja00197a014 . [all data]

Maier and Turner, 1972
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part I. Biphenyls, Faraday Discuss. Chem. Soc., 1972, 54, 149. [all data]

Cotter, Soc. 1965
Cotter, J.L., Electron impact studies of some aromatic fluorocarbons, J. Chem., Soc. 1965, 1520. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,solid	Constant pressure heat capacity of solid
EA	Electron affinity
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
T_boil	Boiling point
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_subH	Enthalpy of sublimation
Δ_vapH	Enthalpy of vaporization

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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