A molecular orbital study of amiloride

Document Type

Article

Publication Date

1-1-1991

Abstract

Molecular orbital calculations with geometry optimization in the 3‐21G(*) basis set were carried out for the acylimino (A, 1a) and the isoimino (E, 1b) tautomers of the free base form of amiloride, and for the protonated form (F, 1c) of amiloride. The results showed the E1 tautomer to be 16.8 kcal/mol higher in energy than the A conformer of lowest energy, A1. The protonation energy of the A1 species was found to be 269.4 kcal/mol. Similar results were obtained using the AM1 method. These results are in agreement with the NMR results of Smith et al. which show the A and F species to be predominant in solution. The 3‐21G(*) rotational barrier for the acylimino tautomer was found to be 19.0 kcal/mol, with the A4 conformer 2.50 kcal/mol higher in energy than the A1. Copyright © 1991 John Wiley & Sons, Inc.

Identifier

1842436073 (Scopus)

Publication Title

Journal of Computational Chemistry

External Full Text Location

https://doi.org/10.1002/jcc.540120710

e-ISSN

1096987X

ISSN

01928651

First Page

850

Last Page

861

Issue

7

Volume

12

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