Document Type

Article

Rights

This item is available under a Creative Commons License for non-commercial use only

Disciplines

Organic Chemistry, Physical chemistry

Publication Details

Biophysical Chemistry, Volume 238, July 2018, Pages 16-21.

https://0-www.sciencedirect.com.ditlib.dit.ie/journal/biophysical-chemistry

Abstract

A 1H NMR study shows the presence of intermolecular hydrogen bonds for AHLs in CDCl3 solution. A detailed computational study of the structure of AHLs and the relative stability between the extended conformations (X) and those showing n→p* interactions (np) have been carried out by means of DFT calculations. Solvent effects have been shown to be very important when stabilising np conformations, particularly with polar solvents. This was shown by the shortening of C···O intramolecular distances and the increase in the relative energies favouring the np conformation with the dielectric constant of the solvent. The charge transfer between the O donor and the acceptor carbonyl group, assessed by second order perturbation energies, E(2), also shows an increase in the E(2) values with the dielectric constant of the solvent.

DOI

10.1016/j.bpc.2018.04.002

Available for download on Sunday, July 26, 2020

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