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
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
• Options:
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR 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 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

Condensed 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

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

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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 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

Ion clustering 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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

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

Free energy of reaction

 +  = ( • )

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

 +  = ( • )

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

Free energy of reaction

 +  = ( • )

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

( • ) +  = ( • 2)

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

 +  = ( • )

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

 +  = ( • )

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

Free energy of reaction

 +  = ( • )

By formula: K⁺ + C₆H₆O = (K⁺ • C₆H₆O)

( • ) +  = ( • 2)

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

 +  = ( • )

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

Free energy of reaction

( • ) +  = ( • 2)

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

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

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR 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]

Andon, Biddiscombe, et al., 1960
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols, J. Chem. Soc., 1960, 5246-5254. [all data]

Parks, Manchester, et al., 1954
Parks, G.S.; Manchester, K.E.; Vaughan, L.M., Heats of combustion and formation of some alcohols, phenols, and ketones, J. Chem. Phys., 1954, 22, 2089-2090. [all data]

Badoche, 1941
Badoche, M., No 19. - Chaleurs de combustion du phenol, du-m-cresol et del leurs ethers; par M. Marius BADOCHE., Bull. Soc. Chim. Fr., 1941, 8, 212-220. [all data]

Kudchadker S.A., 1978
Kudchadker S.A., Ideal gas thermodynamic properties of phenol and cresols, J. Phys. Chem. Ref. Data, 1978, 7, 417-423. [all data]

Evans J.C., 1960
Evans J.C., The vibrational spectra phenol and phenol-OD, Spectrochim. Acta, 1960, 16, 1382-1392. [all data]

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]

Sarin V.N., 1973
Sarin V.N., Thermodynamic properties in the gaseous state of certain monosubstituted benzenes, Thermochim. Acta, 1973, 6, 39-46. [all data]

Ramaswamy V., 1970
Ramaswamy V., Thermo data for n-alkyl phenols, Hydrocarbon Process., 1970, 49, 217-218. [all data]

Andon, Counsell, et al., 1963
Andon, R.J.L.; Counsell, J.F.; Herington, E.F.G.; Martin, J.F., Thermodynamic properties of organic oxygen compounds, Trans. Faraday Soc., 1963, 59, 830-835. [all data]

Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen. J. Am. Chem. Soc., 1933, 55, 2733-2740. [all data]

Nichols and Wads, 1975
Nichols, N.; Wads, I., Thermochemistry of solutions of biochemical model compounds. 3. Some benzene derivatives in aqueous solution, J. Chem. Thermodynam., 1975, 7, 329-336. [all data]

Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A., Study of the heat capacity of selected solvents, Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]

Campbell and Campbell, 1940
Campbell, A.N.; Campbell, A.J.R., The heats of solution, heats of formation, specific heats and equilibrium diagrams of certain molecular compounds. J. Am. Chem. Soc., 1940, 62, 291-297. [all data]

Aoyama and Kanda, 1935
Aoyama, S.; Kanda, E., Studies on the heat capacities at low temperature. Report I. Heat capacities of some organic substances at low temperature, Sci. Rept. Tohoku Imp. Univ. [1]24, 1935, 107-115. [all data]

Andon, Counsell, et al., 1963, 2
Andon, R.J.L.; Counsell, J.F.; Herington, E.F.G.; Martin, J.F., Thermodyn. prop. of organic oxygen compds., part 7- calorimetric study of phenol from 12 to330o K, Trans. Faraday Soc., 1963, 59, 830. [all data]

Delaunois, 1968
Delaunois, C., Effect of the Filling Rate of a Reactor on the Vapor Tension and the Temperature at the Beginning of Cracking of Phenols at High Pressures, Ann. Mines Belg., 1968, No. 1, 9-16. [all data]

Ambrose, 1963
Ambrose, D., Critical Temperatures of Some Phenols and Other Organic Compounds, Trans. Faraday Soc., 1963, 59, 1988. [all data]

Radice, 1899
Radice, G., , Ph. D. Thesis, Univ. of Geneve, 1899. [all data]

Herz and Neukirch, 1923
Herz, W.; Neukirch, E., On Knowldge of the Critical State, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1923, 104, 433-50. [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Parsons, Rochester, et al., 1971
Parsons, G.H.; Rochester, C.H.; Wood, C.E.C., Effect of 4-substitution on the thermodynamics of hydration of phenol and the phenoxide anion, J. Chem. Soc., B:, 1971, 533, https://doi.org/10.1039/j29710000533 . [all data]

Chylinski, Fras, et al., 2001
Chylinski, K.; Fras, Z.; Malanowski, S.K., Vapor-Liquid Equilibrium in Phenol + 2-Ethoxyethanol at 363.15 to 383.15 K, J. Chem. Eng. Data, 2001, 46, 1, 29-33, https://doi.org/10.1021/je0001072 . [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]

Andon, Biddiscombe, et al., 1960, 2
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F., 1009. Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols, J. Chem. Soc., 1960, 5246, https://doi.org/10.1039/jr9600005246 . [all data]

Dykyj, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [all data]

Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A., Vapor Pressure--Temperature Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054 . [all data]

Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A., Physical Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2875-2878, https://doi.org/10.1021/ie50480a053 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Goldblum, Martin, et al., 1947
Goldblum, K.B.; Martin, R.W.; Young, R.B., Vapor Pressure Data for Phenols, Ind. Eng. Chem., 1947, 39, 11, 1474-1476, https://doi.org/10.1021/ie50455a017 . [all data]

Chickos, 1975
Chickos, James Speros, A simple equilibrium method for determining heats of sublimation, J. Chem. Educ., 1975, 52, 2, 134-39, https://doi.org/10.1021/ed052p134 . [all data]

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Sklyarenko, Markin, et al., 1958
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Nitta and Seki, 1948
Nitta, I.; Seki, S., J. Chem. Soc. Jpn. Pure Chem. Sect., 1948, 69, 141. [all data]

Balson, 1947
Balson, E.W., Studies in vapour pressure measurement, Part III.?An effusion manometer sensitive to 5 «65533» 10?6 millimetres of mercury: vapour pressure of D.D.T. and other slightly volatile substances, Trans. Faraday Soc., 1947, 43, 54, https://doi.org/10.1039/tf9474300054 . [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Mastrangelo, 1957
Mastrangelo, S.V.R., Adiabatic calorimeter for determination of cryoscopic data, Anal. Chem., 1957, 29(5), 841-845. [all data]

Inozemtsev, Liakumovich, et al., 1972
Inozemtsev, P.P.; Liakumovich, A.G.; Gracheva, Z.D., Russ. J. Phys. Chem., 1972, 46, 6, 914. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Eykman, 1889
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Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Cp,solid	Constant pressure heat capacity of solid
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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