Benzyl alcohol

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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.

Quantity Value Units Method Reference Comment
Δfgas-94.6 ± 3.0kJ/molCcrPapina, Pimenova, et al., 1995ALS
Δfgas-100.7kJ/molN/AParks, Manchester, et al., 1954Value computed using ΔfHliquid° value of -161.0±1.3 kj/mol from Parks, Manchester, et al., 1954 and ΔvapH° value of 60.3 kj/mol from Papina, Pimenova, et al., 1995.; DRB
Δfgas-113.7kJ/molN/ALandrieu, Baylocq, et al., 1929Value computed using ΔfHliquid° value of -174.0 kj/mol from Landrieu, Baylocq, et al., 1929 and ΔvapH° value of 60.3 kj/mol from Papina, Pimenova, et al., 1995.; DRB
Δfgas-106.7kJ/molN/ASchmidlin, 1906Value computed using ΔfHliquid° value of -167.0 kj/mol from Schmidlin, 1906 and ΔvapH° value of 60.3 kj/mol from Papina, Pimenova, et al., 1995.; DRB

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

Quantity Value Units Method Reference Comment
Δfliquid-154.9 ± 3.0kJ/molCcrPapina, Pimenova, et al., 1995ALS
Δfliquid-161.0 ± 1.3kJ/molCcbParks, Manchester, et al., 1954ALS
Δfliquid-174.kJ/molCcbLandrieu, Baylocq, et al., 1929ALS
Δfliquid-167.kJ/molCcbSchmidlin, 1906ALS
Quantity Value Units Method Reference Comment
Δcliquid-3743.0 ± 2.8kJ/molCcrPapina, Pimenova, et al., 1995Corresponding Δfliquid = -154.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3736.9kJ/molCcbParks, Manchester, et al., 1954Corresponding Δfliquid = -161.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3723.kJ/molCcbLandrieu, Baylocq, et al., 1929Corresponding Δfliquid = -174. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3724.kJ/molCcbBarker, 1925Author was aware that data differs from previously reported values; Corresponding Δfliquid = -174. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3731.kJ/molCcbSchmidlin, 1906Corresponding Δfliquid = -167. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid216.7J/mol*KN/AParks, Todd, et al., 1936Extrapolation below 90 K, 54.06 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
223.6307.5Griigo'ev, Yanin, et al., 1979T = 307 to 461 K. p = 0.98 bar.; DH
215.94298.15Nichols and Wads, 1975DH
217.86298.1Parks, Todd, et al., 1936T = 90 to 300 K.; DH
215.9298.5Smith and Andrews, 1931T = 102 to 299 K. Value is unsmoothed experimental datum.; DH
220.5298.von Reis, 1881T = 290 to 485 K.; DH

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

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

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

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

Quantity Value Units Method Reference Comment
Δr125. ± 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
Δr99.6kJ/molPHPMSCaldwell and Kebarle, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr97.1J/mol*KPHPMSCaldwell and Kebarle, 1986gas phase; M
Δr123.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
Δr86.6 ± 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- • Benzyl alcohol)

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

Quantity Value Units Method Reference Comment
Δr111. ± 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
Δr123.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
Δr74.9 ± 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
Δr1548. ± 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
Δr1520. ± 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 • Benzyl alcohol)

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

Quantity Value Units Method Reference Comment
Δr80.3 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr125.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr43.1 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

By formula: F- + C7H8O = (F- • C7H8O)

Quantity Value Units Method Reference Comment
Δr135.6kJ/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
Δr-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
Δr-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
Δr53.93kJ/molEqkCubberley and Mueller, 1946gas phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, 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]

Barker, 1925
Barker, M.F., Calorific value and constitution, J. Phys. Chem., 1925, 29, 1345-1363. [all data]

Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Moore, W.A., Thermal data on organic compounds. XVI. Some heat capacity, entropy and free energy data for typical benzene derivatives and heterocyclic compounds, J. Am. Chem. Soc., 1936, 58, 398-401. [all data]

Griigo'ev, Yanin, et al., 1979
Griigo'ev, B.A.; Yanin, G.S.; Rastorguev, Yu.L.; Thermophysical parameters of alcohols, Tr. GIAP, 54, 1979, 57-64. [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]

Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H., Thermal energy studies. I. Phenyl derivatives of methane, ethane and some related compounds. J. Am. Chem. Soc., 1931, 53, 3644-3660. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [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]

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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References