Organotin mefenamic complexes—preparations, spectroscopic studies and crystal structure of a triphenyltin ester of mefenamic acid: novel anti‐tuberculosis agents

Abstract

AbstractThe triphenyltin adduct of mefenamic acid, [SnPh3L] (1), the monophenyltin complex [PhSnOL] n (2), and the dibutyltin complex [SnBu2L2] (3), where HL is 2‐[bis(2,3‐dimethylphenyl)amino]benzoic acid (mefenamic acid), have been prepared and structurally characterized by means of vibrational, 1H and 13C NMR spectroscopies. The crystal structure of 1 has been determined by X‐ray crystallography. X‐ray analysis revealed a pseudo‐pentacoordinated structure containing Ph3Sn coordinated to the carboxylato group. The structural distortion is a displacement from the tetrahedron toward the trigonal bipyramid. Significant CH–π interactions and intramolecular hydrogen bonds stabilize the structure 1. The polar imino hydrogen atom participates in intramolecular hydrogen bonds. Complex 1 is self‐assembled via CH–π and stacking interactions. Vibrational and NMR data are discussed in terms of the crystal structure and the proposed structures for 1–3. Compounds 1 and 3 were tested for antimycobacterial activity against Mycobacterium tuberculosis H37Rv. Copyright © 2002 John Wiley & Sons, Ltd.