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Benzyl alcohol

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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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

C7H7O- + Benzyl alcohol = (C7H7O- bullet Benzyl alcohol)

By formula: C7H7O- + C7H8O = (C7H7O- bullet C7H8O)

Quantity Value Units Method Reference Comment
Deltar125. ± 10.kJ/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Deltar99.6kJ/molPHPMSCaldwell and Kebarle, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar97.1J/mol*KPHPMSCaldwell and Kebarle, 1986gas phase; M
Deltar123.J/mol*KN/ACaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Deltar86.6 ± 6.7kJ/molTDAsCaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M

C8H5- + Benzyl alcohol = (C8H5- bullet Benzyl alcohol)

By formula: C8H5- + C7H8O = (C8H5- bullet C7H8O)

Quantity Value Units Method Reference Comment
Deltar111. ± 12.kJ/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Quantity Value Units Method Reference Comment
Deltar123.J/mol*KN/ACaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Deltar74.9 ± 8.4kJ/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M

C7H7O- + Hydrogen cation = Benzyl alcohol

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Deltar1548. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1520. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

cyclopentadienide anion + Benzyl alcohol = (cyclopentadienide anion bullet Benzyl alcohol)

By formula: C5H5- + C7H8O = (C5H5- bullet C7H8O)

Quantity Value Units Method Reference Comment
Deltar80.3 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar125.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar43.1 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

Fluorine anion + Benzyl alcohol = (Fluorine anion bullet Benzyl alcohol)

By formula: F- + C7H8O = (F- bullet C7H8O)

Quantity Value Units Method Reference Comment
Deltar135.6kJ/molN/AMihalick, Gatev, et al., 1996gas phase; affinity derived using a ROH..F. neutral binding energy of 10.3 kcal/mol.; B

Benzene, (iodomethyl)- + Water = Hydrogen iodide + Benzyl alcohol

By formula: C7H7I + H2O = HI + C7H8O

Quantity Value Units Method Reference Comment
Deltar-12.6kJ/molCmGellner and Skinner, 1949liquid phase; Heat of hydrolysis; ALS

Benzene, (bromomethyl)- + Water = Hydrogen bromide + Benzyl alcohol

By formula: C7H7Br + H2O = HBr + C7H8O

Quantity Value Units Method Reference Comment
Deltar-7.9kJ/molCmGellner and Skinner, 1949liquid phase; Heat of hydrloysis; ALS

Benzyl alcohol = Benzaldehyde + Hydrogen

By formula: C7H8O = C7H6O + H2

Quantity Value Units Method Reference Comment
Deltar53.93kJ/molEqkCubberley and Mueller, 1946gas phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

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

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]

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]

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]

Gellner and Skinner, 1949
Gellner, O.H.; Skinner, H.A., Dissociation energies of carbon-halogen bonds. The bond strengths allyl-X and benzyl-X, J. Chem. Soc., 1949, 1145-1148. [all data]

Cubberley and Mueller, 1946
Cubberley, A.H.; Mueller, M.B., Equilibrium studies on the dehydrogenation of primary and secondary alcohols. I. 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol, J. Am. Chem. Soc., 1946, 68, 1149-1151. [all data]


Notes

Go To: Top, Reaction thermochemistry data, References