Estimation of mesogenic character of disubstituted pyridine derivatives on the basis of intermolecular interaction energy calculations

Abstract

Two pyridine derivative “2-(4-butoxyphenyl)-5-hexyl pyridine” (Cpd 1) and “3-(4-butoxyphenyl)-6-hexyl pyridine” (Cpd 2) differing only in the relative position of nitrogen have been examined quantum mechanically to understand the possible reason of their different mesogenic character. The studies include geometry optimization, evaluation of interaction energy between a molecular pair at minimum energy configuration and tendency of ordering at various interacting conditions. It has been found that in Cpd 1, the phenyl and pyridine rings are almost coplanar with the butoxy tail while Cpd 2 differs significantly from planarity. Cpd 1 therefore stacks more closely than Cpd 2. An attempt has been made to correlate the results of intermolecular interaction energy calculation with the mesogenic behavior of the respective molecules.