Diphenylacetylene

Formula: C₁₄H₁₀
Molecular weight: 178.2292
IUPAC Standard InChI: InChI=1S/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H
IUPAC Standard InChIKey: JRXXLCKWQFKACW-UHFFFAOYSA-N
CAS Registry Number: 501-65-5
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: Diphenylethyne; Benzene, 1,1'-(1,2-ethynediyl)bis-; Acetylene, diphenyl-; Ethyne, diphenyl-; Tolan; Tolane; 1,2-Diphenylacetylene; 1,1'-(1,2-Ethanediyl)bisbenzene; NSC 5185
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
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	385. ± 2.7	kJ/mol	Chyd	Davis, Allinger, et al., 1985	ALS
Quantity	Value	Units	Method	Reference	Comment
S°_gas	452.	J/mol*K	N/A	Alcolea Palafox M., 1996	This value was calculated by semiempirical AM1 method. According to estimation by difference method [ Dorofeeva O.V., 1997] it could be overestimated by 15-30 J/mol*K.; GT

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	-7250. ± 1.	kJ/mol	Ccb	Coops, Hoijtink, et al., 1953	Corresponding Δ_fHº_solid = 312. 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
297.5	340.	Kurbatov, 1950	T = 65 to 303°C. Mp 61°C.; DH
225.9	298.5	Smith and Andrews, 1931	T = 102 to 323 K. Value is unsmoothed experimental datum.; DH

Gas phase ion energetics data

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Data evaluated as indicated in comments:
L - Sharon G. Lias

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

View reactions leading to C₁₄H₁₀⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	7.94 ± 0.03	eV	N/A	N/A	L

Electron affinity determinations

EA (eV)	Method	Reference	Comment
<0.321 ± 0.074	ECD	Wojnarovits and Foldiak, 1981	G3MP2B3 calculations indicate an EA of ca. 0.2 eV; B

Ionization energy determinations

IE (eV)	Method	Reference	Comment
7.95 ± 0.08	PE	Elbel, Lienert, et al., 1981	LLK
7.90 ± 0.02	PE	Maier and Turner, 1973	LLK
8.0 ± 0.05	PE	Eland, 1972	LLK
7.91	PE	Rowland, 1971	Unpublished result of J.H.D. Eland; LLK
23.4 ± 0.1	EI	Natalis and Franklin, 1965	RDSH
8.85 ± 0.05	EI	Natalis and Franklin, 1965	RDSH

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₆H₅⁺	20.7 ± 0.1	?	EI	Natalis and Franklin, 1965	RDSH
C₈H₆⁺	17.8 ± 0.1	?	EI	Natalis and Franklin, 1965	RDSH
C₉H₅⁺	21.3 ± 0.2	?	EI	Natalis and Franklin, 1965	RDSH
C₉H₇⁺	17.5 ± 0.1	?	EI	Natalis and Franklin, 1965	RDSH
C₁₀H₆⁺	18.2 ± 0.1	2C₂H₂	EI	Natalis and Franklin, 1965	RDSH
C₁₁H₇⁺	17.5 ± 0.1	?	EI	Natalis and Franklin, 1965	RDSH
C₁₂H₇⁺	17.46 ± 0.06	?	EI	Natalis and Franklin, 1965	RDSH
C₁₂H₈⁺	15.58 ± 0.05	?	EI	Natalis and Franklin, 1965	RDSH
C₁₂H₈₂⁺	20.5 ± 0.1	?	EI	Natalis and Franklin, 1965	RDSH
C₁₄H₈⁺	16.66 ± 0.05	H₂	EI	Natalis and Franklin, 1965	RDSH
C₁₄H₉⁺	15.1 ± 0.1	H	EI	Natalis and Franklin, 1965	RDSH

References

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Davis, Allinger, et al., 1985
Davis, H.E.; Allinger, N.L.; Rogers, D.W., Enthalpies of hydrogenation of phenylalkynes: indirect determination of the enthalpy of formation of diphenylcyclopropenone, J. Org. Chem., 1985, 50, 3601-3604. [all data]

Alcolea Palafox M., 1996
Alcolea Palafox M., Vibrational spectra and structure of diphenylacetylenes, Spectrosc. Lett., 1996, 29, 241-266. [all data]

Dorofeeva O.V., 1997
Dorofeeva O.V., Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]

Coops, Hoijtink, et al., 1953
Coops, J.; Hoijtink, G.J.; Kramer, Th.J.E.; Faber, A.C., Thermochemical investigations on arylethynes I. Heats of combustion of some diarylethynes, Rec. Trav. Chim. Pays/Bas, 1953, 72, 781. [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]

Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G., Electron capture detection of aromatic hydrocarbons, J. Chromatogr. Sci., 1981, 206, 511. [all data]

Elbel, Lienert, et al., 1981
Elbel, S.; Lienert, K.; Krebs, A.; tom Dieck, H., Phenylethin - mustersonde fur substituenteneffekte, Liebigs Ann. Chem., 1981, 1785. [all data]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part 2. Phenylethylenes, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 196. [all data]

Eland, 1972
Eland, J.H.D., Photoelectron spectra and ionization potentials of aromatic hydrocarbons, Int. J. Mass Spectrom. Ion Phys., 1972, 9, 214. [all data]

Rowland, 1971
Rowland, C.G., Kinetic energy distributions of C₁₂H₈ fragment ions in the mass spectra of anthracene, phenanthrene and diphenylacetylene, Intern. J. Mass Spectrom. Ion Phys., 1971, 7, 79. [all data]

Natalis and Franklin, 1965
Natalis, P.; Franklin, J.L., Ionization and dissociation of diphenyl and condensed ring aromatics by electron impact. I. Biphenyl, diphenylacetylene, and phenanthrene, J. Phys. Chem., 1965, 69, 2935. [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
IE (evaluated)	Recommended ionization energy
S°_gas	Entropy of gas 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

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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