Theoretical Studies of Substituted Naphthylcarbinyl Cations and Associated Correlation Analysis

Document Type

Article

Publication Date

1-1-1982

Abstract

Minimal basis set ab initio calculations are performed on naphthalenes and naphthalenecarbinyl cations substituted by CH3, F, CF3, CN, CH3O, NH2, and NO2. Suitable substitution reverses the inherent stability of a 1-naphthylcarbinyl cation over a 2-naphthylcarbinyl cation. Homodesmotic stabilization energies are correlated according to a modified Dewar-Grisdale equation as well as Taft's dual substituent parameter (DSP) equation, and the results are compared with published experimental data and corresponding treatments for benzyl cations. © 1982, American Chemical Society. All rights reserved.

Identifier

22744434286 (Scopus)

Publication Title

Journal of Organic Chemistry

External Full Text Location

https://doi.org/10.1021/jo00137a010

e-ISSN

15206904

ISSN

00223263

First Page

3076

Last Page

3081

Issue

16

Volume

47

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