Synthesis, spectroscopic and structural studies of new Schiff bases prepared from 3,5-Bu-2(t)-salicylaldehyde and heterocyclic amines: X-ray structure of N-(3,5-di-tert-butylsalicylidene)-1-ethylcarboxylato-4-aminopiperidine

Abstract

Two new sterically hindered salicylaldimines, N-(2,2,6,6-tetramethyl-piperidine-4)-3,5-Bu(2)(t-)salicylaldimine (I) and N-(1-carboxyethyl 2 piperidine-4)-3,5-Bu-2(t)-salicylaldimine (II), have been prepared and characterized by IR, UV-vis, H-1 NMR, C-13 NMR techniques and the structure of II has been examined by X-ray crystallography. No intermolecular H-bonding, pi-pi stacking or C-H center dot center dot center dot pi interactions are observed in the structure. The crystal structure the was mainly governed by intermolecular steric repulsions, due to bulky tert-butyl groups and the tendency of salicylaldimine rings to pack in parallel mode forms one-dimensional columns. (C) 2007 Published by Elsevier B.V.