Phenol

• Formula: C₆H₆O
• Molecular weight: 94.1112
• IUPAC Standard InChI: InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H Copy

  
• IUPAC Standard InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-95-2
• 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.
• Isotopologues:
  • Phenol-d6-
• Other names: Carbolic acid; Baker's P and S Liquid and Ointment; Benzenol; Hydroxybenzene; Izal; Monohydroxybenzene; Monophenol; Oxybenzene; Phenic acid; Phenyl alcohol; Phenyl hydrate; Phenyl hydroxide; Phenylic acid; Phenylic alcohol; PhOH; Benzene, hydroxy-; Acide carbolique; Baker's P & S liquid & Ointment; Fenol; Fenolo; NCI-C50124; Paoscle; Phenole; Carbolsaure; NA 2821; Phenol alcohol; Phenol, molten; Rcra waste number U188; UN 1671; UN 2312; UN 2821; Phenic alcohol; NSC 36808; Campho-Phenique Cold Sore Gel (Salt/Mix); Campho-Phenique Gel (Salt/Mix); Campho-Phenique Liquid (Salt/Mix)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Ion clustering data
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
MS - José A. Martinho Simões

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

 +  =

By formula: C₆H₅O^- + H⁺ = C₆H₆O

 +  = ( • )

By formula: Cl^- + C₆H₆O = (Cl^- • C₆H₆O)

Free energy of reaction

 +  = ( • )

By formula: F^- + C₆H₆O = (F^- • C₆H₆O)

 +  = ( • )

By formula: Br^- + C₆H₆O = (Br^- • C₆H₆O)

Free energy of reaction

 +  = ( • )

By formula: I^- + C₆H₆O = (I^- • C₆H₆O)

Free energy of reaction

 +  = ( • )

By formula: C₂H₃O₂^- + C₆H₆O = (C₂H₃O₂^- • C₆H₆O)

 +  = ( • )

By formula: Na⁺ + C₆H₆O = (Na⁺ • C₆H₆O)

Free energy of reaction

 +  =  + 

By formula: C₆H₆O + C₁₂H₁₈O = C₉H₁₂O + C₉H₁₂O

C₂₂H₂₀O₂Ti (cr) + 2( • 5.55) (solution) = 2 (cr) +  (cr)

By formula: C₂₂H₂₀O₂Ti (cr) + 2(HCl • 5.55H₂O) (solution) = 2C₆H₆O (cr) + C₁₀H₁₀Cl₂Ti (cr)

 (solution) + C₅H₁₁BrMg (solution) = C₆H₅BrMgO (solution) +  (solution)

By formula: C₆H₆O (solution) + C₅H₁₁BrMg (solution) = C₆H₅BrMgO (solution) + C₅H₁₂ (solution)

C₂₀H₃₂Zr (solution) +  (solution) = C₂₆H₃₆OZr (solution) +  (g)

By formula: C₂₀H₃₂Zr (solution) + C₆H₆O (solution) = C₂₆H₃₆OZr (solution) + H₂ (g)

C₂₆H₃₆OZr (solution) +  (solution) = C₃₂H₄₀O₂Zr (solution) +  (g)

By formula: C₂₆H₃₆OZr (solution) + C₆H₆O (solution) = C₃₂H₄₀O₂Zr (solution) + H₂ (g)

 +  =  + 

By formula: C₈H₈O₂ + H₂O = C₆H₆O + C₂H₄O₂

 +  =  + 

By formula: C₆H₆O + C₁₄H₂₂O = C₁₀H₁₄O + C₁₀H₁₄O

 + C₁₈H₃₀O =  + 

By formula: C₆H₆O + C₁₈H₃₀O = C₁₄H₂₂O + C₁₀H₁₄O

 +  =  + 

By formula: C₆H₆O + C₁₄H₂₂O = C₁₀H₁₄O + C₁₀H₁₄O

 +  = 2

By formula: C₆H₆O + C₁₄H₂₂O = 2C₁₀H₁₄O

C₆H₅NaO (cr) + ( • 552) (solution) =  (cr) +  (cr)

By formula: C₆H₅NaO (cr) + (HCl • 552H₂O) (solution) = C₆H₆O (cr) + ClNa (cr)

 +  =  + 

By formula: C₆H₆O + C₁₄H₂₂O = C₁₀H₁₄O + C₁₀H₁₄O

 +  =  + 

By formula: C₆H₆O + C₁₄H₂₂O = C₁₀H₁₄O + C₁₀H₁₄O

( • ) +  = ( • 2)

By formula: (Li⁺ • C₆H₆O) + C₆H₆O = (Li⁺ • 2C₆H₆O)

( • ) +  = ( • 2)

By formula: (Na⁺ • C₆H₆O) + C₆H₆O = (Na⁺ • 2C₆H₆O)

( • ) +  = ( • 2)

By formula: (Cs⁺ • C₆H₆O) + C₆H₆O = (Cs⁺ • 2C₆H₆O)

( • ) +  = ( • 2)

By formula: (Rb⁺ • C₆H₆O) + C₆H₆O = (Rb⁺ • 2C₆H₆O)

( • ) +  = ( • 2)

By formula: (K⁺ • C₆H₆O) + C₆H₆O = (K⁺ • 2C₆H₆O)

 (cr) + C₁₀H₁₁ClZr (cr) = C₁₆H₁₅ClOZr (cr) +  (g)

By formula: C₆H₆O (cr) + C₁₀H₁₁ClZr (cr) = C₁₆H₁₅ClOZr (cr) + H₂ (g)

 +  = 2

By formula: C₆H₆O + C₁₄H₂₂O = 2C₁₀H₁₄O

 +  =  + 

By formula: C₆H₆O + C₁₄H₂₂O = C₁₀H₁₄O + C₁₀H₁₄O

C₆H₅NaO (cr) +  (l) =  (cr) +  (cr)

By formula: C₆H₅NaO (cr) + H₂O (l) = C₆H₆O (cr) + HNaO (cr)

 +  = ( • )

By formula: Li⁺ + C₆H₆O = (Li⁺ • C₆H₆O)

 +  = ( • )

By formula: Cs⁺ + C₆H₆O = (Cs⁺ • C₆H₆O)

 +  = ( • )

By formula: Rb⁺ + C₆H₆O = (Rb⁺ • C₆H₆O)

 +  = ( • )

By formula: K⁺ + C₆H₆O = (K⁺ • C₆H₆O)

=  + 

By formula: C₁₀H₁₄O = C₄H₈ + C₆H₆O

=  + 

By formula: C₁₀H₁₄O = C₄H₈ + C₆H₆O

=  + 

By formula: C₁₀H₁₄O = C₆H₆O + C₄H₈

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₆H₆O⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

 +  =

By formula: C₆H₅O^- + H⁺ = C₆H₆O

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% IN CCl4 FOR 3800-1300, 10% IN CS2 FOR 1300-650, 10% IN CCl4 FOR 650-250 CM^-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

UV/Visible spectrum

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Cox, 1961
Cox, J.D., The heats of combustion of phenol and the three cresols, Pure Appl. Chem., 1961, 2, 125-128. [all data]

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Green J.H.S., 1961
Green J.H.S., The thermodynamic properties of organic oxygen compounds. II. Vibrational assignment and calculated thermodynamic properties of phenol, J. Chem. Soc., 1961, 2236-2241. [all data]

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Capponi, Gut, et al., 1999
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Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N., The photoionization of the vapors of certain organic compounds, Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]

Ballard, Jones, et al., 1987
Ballard, R.E.; Jones, J.; Read, D.; Inchley, A.; Cranmer, M., He(I) photoelectron studies of liquids and gases, Chem. Phys. Lett., 1987, 137, 125. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Speirs, M.; Ridyard, J.N.A., The electronic structure of substituted benzenes; ab initio calculations and photoelectron spectra for phenol, the methyl- and fluoro-derivatives, and the dihydroxybenzenes, J. Mol. Struct., 1979, 52, 293. [all data]

Kobayashi, 1978
Kobayashi, T., A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes, Phys. Lett., 1978, 69, 105. [all data]

Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S., Photoelectron spectra of substituted benzenes, Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]

Dewar, Ernstbrunner, et al., 1974
Dewar, P.S.; Ernstbrunner, E.; Gilmore, J.R.; Godfrey, M.; Mellor, J.M., Conformational analysis of alkyl aryl ethers and alkyl aryl sulphides by photoelectron spectroscopy, Tetrahedron, 1974, 30, 2455. [all data]

Tajima and Tsuchiya, 1973
Tajima, S.; Tsuchiya, T., Energetics consideration of C₅H₅⁺ ions produced from various precursors by electron impact, Bull. Chem. Soc. Jpn., 1973, 46, 3291. [all data]

Occolowitz and White, 1968
Occolowitz, J.L.; White, G.L., Energetic considerations in the assignment of some fragment ion structures, Australian J. Chem., 1968, 21, 997. [all data]

Lifshitz and Malinovich, 1984
Lifshitz, C.; Malinovich, Y., Time resolved photoionization mass spectrometry in the millisecond range, Int. J. Mass Spectrom. Ion Processes, 1984, 60, 99. [all data]

Howe and Williams, 1969
Howe, I.; Williams, D.H., Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes, J. Am. Chem. Soc., 1969, 91, 7137. [all data]

Martynoff, 1949
Martynoff, M., Note de laboratoire: Spectres d'absorption de quelques p-quinones, Bull. Soc. Chim. Fr., 1949, 16, 258-261. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  IE (evaluated)	Recommended ionization energy
  T	Temperature
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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