o-Hydroxybiphenyl

Formula: C₁₂H₁₀O
Molecular weight: 170.2072
IUPAC Standard InChI: InChI=1S/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H
IUPAC Standard InChIKey: LLEMOWNGBBNAJR-UHFFFAOYSA-N
CAS Registry Number: 90-43-7
Chemical structure:
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Other names: [1,1'-Biphenyl]-2-ol; 2-Biphenylol; o-Biphenylol; o-Diphenylol; o-Hydroxydiphenyl; o-Phenylphenol; o-Xenol; Biphenyl-2-ol; Dowicide 1; Phenol, o-phenyl-; 2-Phenylphenol; Preventol O extra; Remol TRF; 2-Hydroxybiphenyl; 2-Hydroxydiphenyl; o-Phenylphenol, cosmetic grade; Biphenyl, 2-hydroxy-; NCI-C50351; Torsite; Tumescal OPE; USAF EK-2219; 1-Hydroxy-2-phenylbenzene; 2-Hydroxybifenyl; Dowicide 1 antimicrobial; 2-Fenylfenol; Kiwi lustr 277; OPP; Orthohydroxydiphenyl; Orthophenylphenol; Orthoxenol; Tetrosin OE; Nectryl; Anthrapole 73; 2-Hydroxy-1,1'-biphenyl; Invalon OP; Tetrosin OE-N; (1,1-Biphenyl)-2-ol; Hydroxy-2-phenylbenzene; Nipacide OPP; Phenylphenol; Phenylphenol (ortho-); NSC 1548; Preventol 3041
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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	17.	kJ/mol	Ccb	Bertholon, Giray, et al., 1971

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_fH°_solid	-88.	kJ/mol	Ccb	Bertholon, Giray, et al., 1971	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-6063.	kJ/mol	Ccb	Bertholon, Giray, et al., 1971	Corresponding Δ_fHº_solid = -88. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	261.75	J/mol*K	N/A	Geidarov, Dzhafarov, et al., 1973	DH
S°_{solid,1 bar}	261.75	J/mol*K	N/A	Geidarov, Karasharli, et al., 1977	DH

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
227.61	298.15	Geidarov, Karasharli, et al., 1977	Based on previously published work of authors, not available in detail, on Cp 12 to 370 K.; DH
235.10	298.15	Geidarov, Dzhafarov, et al., 1973	T = 12 to 350 K. Complete Cp data in paper deposited at VINITI, No. 4748-72, 24 Aug, 1972.; DH

Gas phase ion energetics data

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Data compiled by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₁₂H₁₀O⁺ (ion structure unspecified)

Ionization energy determinations

IE (eV)	Method	Reference
7.80 ± 0.02	PE	Maier and Turner, 1972

References

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Bertholon, Giray, et al., 1971
Bertholon, G.; Giray, M.; Perrin, R.; Vincent-Falquet-Berny, M.F., No. 532. - Etude physicochimique des phenols. OX. - Ethanlpies de combustion et energies de resonance des alcoyl et aryphenols, Bull. Soc. Chim. France, 1971, 3180-3187. [all data]

Geidarov, Dzhafarov, et al., 1973
Geidarov, Kh.I.; Dzhafarov, O.I.; Karasharli, K.A.; Kostryukov, V.N., Thermodynamics of o-hydroxybiphenyl at low temperatures, Zhur. Fiz. Khim., 1973, 47, 275. [all data]

Geidarov, Karasharli, et al., 1977
Geidarov, Kh.I.; Karasharli, K.A.; Dzhafarov, O.I., Analysis of the results of the thermodynamic investigation of diphenyl derivatives, Azerb. Khim. Zhur., 1977, (5), 112-115. [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]

Notes

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Symbols used in this document:

C_p,solid	Constant pressure heat capacity of solid
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
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

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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