Resonance and field/inductive substituent effects on the gas‐phase acidities of  para ‐substituted phenols: a direct approach employing density functional theory | Zendy

Barbour Josiah B. | Zendy; Karty Joel M. | Zendy

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Resonance and field/inductive substituent effects on the gas‐phase acidities of para ‐substituted phenols: a direct approach employing density functional theory

Author(s) -

Barbour Josiah B.,

Karty Joel M.

Publication year - 2005

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.850

Subject(s) - substituent , chemistry , inductive effect , phenols , resonance (particle physics) , phenol , density functional theory , computational chemistry , gas phase , molecule , stereochemistry , medicinal chemistry , organic chemistry , physics , particle physics

Relative gas‐phase acidities of para ‐substituted phenols ( 1 , Sub—C 6 H 4 —OH) and their ω‐substituted para ‐alkylphenol analogs [ 2 , Sub—(CH 2 ) n —C 6 H 4 —OH] were calculated at the B3LYP/6–31+G* and AM1 levels of theory. The acidity of a substituted molecule of 2 is compared with that of the unsubstituted molecule of 2 to determine the field/inductive effect of the substituent on the acidity of 2 . This field/inductive effect was extrapolated to n = 0, yielding the field/inductive effect of the substituent on the acidity of 1 . The derived field/inductive effect in 1 was subtracted from the difference in acidity between 1 and phenol in order to determine the resonance effect of the substituent on the acidity of 1 . Our results are compared with the field/inductive and resonance substituent parameters empirically derived from previous experimental solution studies. Copyright © 2004 John Wiley & Sons, Ltd.

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