Abstract
A series of six N-phthaloyl aminocarboxylic acids were synthesized by using improved microwave irradiation with a multimode reactor. X-ray single crystal diffraction established the molecular structure of three N-protected aminocarboxylic acids derivatives, and spectral data agree with these in solution. The hydrogen bonding characteristics of this class of molecules are discussed on the basis of crystal structural analyses, MP2/DFT quantum calculations and Hirshfeld surfaces analyses. The relative strengths of the structural O-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonding chain and ring motifs are compared. Antimicrobial activities of 2-(1,3-dioxoisoindolin-2-yl)propanoic acid, 2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoic acid and 2-(4-(1,3-dioxoisoindolin-2-yl)phenyl)acetic acid, were screened against three pathogenic strains; only the first two compounds were found to be quite sensitive against Gram +ve and Gram -ve bacterial strains, respectively. A relative structure-function relationship is observed. (c) 2011 Elsevier B.V. All rights reserved.