Benzyl alcohol

• Formula: C₇H₈O
• Molecular weight: 108.1378
• IUPAC Standard InChI: InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2 Copy

  
• IUPAC Standard InChIKey: WVDDGKGOMKODPV-UHFFFAOYSA-N Copy
• CAS Registry Number: 100-51-6
• 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: Benzenemethanol; α-Hydroxytoluene; α-Toluenol; (Hydroxymethyl)benzene; Benzenecarbinol; Phenylcarbinol; Phenylmethanol; Phenylmethyl alcohol; Methanol, phenyl-; NCI-C06111; Hydroxytoluene; Bentalol; Benzoyl alcohol; Benzenmethanol; Benzylic alcohol; Methanol benzene; NSC 8044; Benzyl Alkohol
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• Information on this page:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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.

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

Data compiled as indicated in comments:
B - John E. Bartmess
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
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C₇H₈O⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₇H₇O^- +  =

By formula: C₇H₇O^- + H⁺ = C₇H₈O

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

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: C₅H₅^- + C₇H₈O = (C₅H₅^- • C₇H₈O)

C₇H₇O^- +  = (C₇H₇O^- • )

By formula: C₇H₇O^- + C₇H₈O = (C₇H₇O^- • C₇H₈O)

C₈H₅^- +  = (C₈H₅^- • )

By formula: C₈H₅^- + C₇H₈O = (C₈H₅^- • C₇H₈O)

 +  = ( • )

By formula: F^- + C₇H₈O = (F^- • C₇H₈O)

Mass spectrum (electron ionization)

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

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Notes

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

Papina, Pimenova, et al., 1995
Papina, T.S.; Pimenova, S.M.; Luk'yanova, V.A.; Kolesov, V.P., Standard enthalpies of formation of benzyl alcohol and α,α,α-trichlorotoluene, Russ. J. Phys. Chem. (Engl. Transl.), 1995, 69, 1951-1953, In original 2148. [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]

Landrieu, Baylocq, et al., 1929
Landrieu, P.; Baylocq, F.; Johnson, J.R., Etude thermochimique dans la serie furanique, Bull. Soc. Chim. France, 1929, 45, 36-49. [all data]

Schmidlin, 1906
Schmidlin, M.J., Recherches chimiques et thermochimiques sur la constitution des rosanilines, Ann. Chim. Phys., 1906, 1, 195-256. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Selim, Rabbih, et al., 1987
Selim, E.T.; Rabbih, M.A.; Fahmey, M.A., M and [M-1]⁺ ions formed for benzyl alcohol, benzyl amine and benzyl cyanide, Org. Mass Spectrom., 1987, 22, 381. [all data]

Russell, Freiser, et al., 1983
Russell, D.H.; Freiser, B.S.; McBay, E.H.; Canada, D.C., The structure of decomposing [C₇H₇O]⁺ ions: Benzyl versus tropylium ion structures, Org. Mass Spectrom., 1983, 18, 474. [all data]

Gilbert, Leach, et al., 1973
Gilbert, J.R.; Leach, W.P.; Miller, J.R., Ionisation appearance potential measurements in arene chromium tricarbonyls, J. Organomet. Chem., 1973, 49, 219. [all data]

Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G., Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH₂-R, Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [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]

Deshmukh, Dutta, et al., 1982
Deshmukh, P.; Dutta, T.K.; Hwang, J.L.-S.; Housecroft, C.E.; Fehlner, T.P., Photoelectron spectroscopic measurements of the relative charge on carbyne fragments bound to polynuclear cobalt carbonyl clusters, J. Am. Chem. Soc., 1982, 104, 1740. [all data]

Eck, Schweig, et al., 1978
Eck, V.; Schweig, A.; Vermeer, H., The ultraviolet photoelectron spectrum of o-benzoquinone methide, Tetrahedron Lett., 1978, 27, 2433. [all data]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Selim, Rabbih, et al., 1989
Selim, E.T.M.; Rabbih, M.A.; Fahmey Ahmad, M.A.; Shalbi, A.S., Energetic study of [C₅H₃]⁺ fragment ion produced from some benzyl derivatives, Arab Gulf J. Sci. Res., 1989, 7, 53. [all data]

Selim, Rabbih, et al., 1987, 2
Selim, E.T.M.; Rabbih, M.A.; Fahmey, M.A., A mass spectrometric study of [C₇H₇]⁺ and [C₆H₇]⁺ fragment ions obtained from benzyl alcohol, benzyl amine and benzyl cyanide, Egypt. J. Phys., 1987, 18, 37. [all data]

Harrison, Haynes, et al., 1965
Harrison, A.G.; Haynes, P.; McLean, S.; Meyer, F., The mass spectra of methyl-substituted cyclopentadienes, J. Am. Chem. Soc., 1965, 87, 5099. [all data]

Selim, Rabbih, et al., 1987, 3
Selim, E.T.; Rabbih, M.A.; Rezk, A.M.H.; Fahmey, M.A., Energetics of [C₇H₆]⁺ fragment ion using electron impact technique, Indian J. Pure Appl. Phys., 1987, 25, 451. [all data]

Meyerson, Rylander, et al., 1959
Meyerson, S.; Rylander, P.N.; Eliel, E.L.; McCollum, J.D., Organic ions in the gas phase. VII. Tropylium ion from benzyl chloride and benzyl alcohol, J. Am. Chem. Soc., 1959, 81, 2606. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Meot-ner, 1988
Meot-ner, M., The Ionic Hydrogen Bond and Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules, J. Am. Chem. Soc., 1988, 110, 12, 3858, https://doi.org/10.1021/ja00220a022 . [all data]

Caldwell, Rozeboom, et al., 1984
Caldwell, G.; Rozeboom, M.D.; Kiplinger, J.P.; Bartmess, J.E., Anion-alcohol hydrogen bond strengths in the gas phase, J. Am. Chem. Soc., 1984, 106, 4660. [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Thermodynamics of the Association Reactions OH- - H2O = HOHOH- and CH3O- - CH3OH = CH3OHOCH3- in the Gas Phase, J. Phys. Chem., 1990, 94, 12, 5184, https://doi.org/10.1021/j100375a076 . [all data]

Meot-ner and Sieck, 1986
Meot-ner, M.; Sieck, L.W., Relative acidities of water and methanol, and the stabilities of the dimer adducts, J. Phys. Chem., 1986, 90, 6687. [all data]

Caldwell and Kebarle, 1986
Caldwell, G.; Kebarle, P., Mobility of Gaseous Ions in Weak Electric Fields in Unpublished results, 1986. [all data]

Meot-Ner(Mautner), 1986
Meot-Ner(Mautner), M., Comparative Stabilities of Cationic and Anionic Hydrogen-Bonded Networks. Mixed Clusters of Water-Methanol, J. Am. Chem. Soc., 1986, 108, 20, 6189, https://doi.org/10.1021/ja00280a014 . [all data]

Mihalick, Gatev, et al., 1996
Mihalick, J.E.; Gatev, G.G.; Brauman, J.I., Electron Photodetachment Spectroscopy of Solvated Anions: RO.HF- or ROH.F-?, J. Am. Chem. Soc., 1996, 118, 49, 12424, https://doi.org/10.1021/ja954202k . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  AE	Appearance energy
  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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