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Phenol, 4-chloro-

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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 compiled as indicated in comments:
B - John E. Bartmess
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C6H5ClO+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
9.07EICrable and Kearns, 1962RDSH
8.69PEBaker, May, et al., 1968Vertical value; RDSH

De-protonation reactions

C6H4ClO- + Hydrogen cation = Phenol, 4-chloro-

By formula: C6H4ClO- + H+ = C6H5ClO

Quantity Value Units Method Reference Comment
Deltar1435. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; Exptl «DELTA»Hf(AH) more stable than group additivity by ca. 8 kcal/mol; value altered from reference due to change in acidity scale; B
Deltar1438. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1407. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; Exptl «DELTA»Hf(AH) more stable than group additivity by ca. 8 kcal/mol; value altered from reference due to change in acidity scale; B
Deltar1409. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

References

Go To: Top, Gas phase ion energetics data, Notes

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

Crable and Kearns, 1962
Crable, G.F.; Kearns, G.L., Effect of substituent groups on the ionization potentials of benzenes, J. Phys. Chem., 1962, 66, 436. [all data]

Baker, May, et al., 1968
Baker, A.D.; May, D.P.; Turner, D.W., Molecular photoelectron spectroscopy. Part VII. The vertical ionisation potentials of benzene and some of its monosubstituted and 1,4-disubstituted derivatives, J. Chem. Soc. B, 1968, 22. [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [all data]


Notes

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