Organotin mefenamic complexes—preparations, spectroscopic studies and crystal structure of a triphenyltin ester of mefenamic acid: novel anti-tuberculosis agents
✍ Scribed by Dimitra Kovala-Demertzi; Vaso Dokorou; Zbigniew Ciunik; Nikolaos Kourkoumelis; Mavroudis A. Demertzis
- Publisher
- John Wiley and Sons
- Year
- 2002
- Tongue
- English
- Weight
- 185 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0268-2605
- DOI
- 10.1002/aoc.308
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✦ Synopsis
The triphenyltin adduct of mefenamic acid, [SnPh 3 L] (1), the monophenyltin complex [PhSnOL] n (2), and the dibutyltin complex [SnBu 2 L 2 ] (3), where HL is 2-[bis(2,3-dimethylphenyl)amino]benzoic acid (mefenamic acid), have been prepared and structurally characterized by means of vibrational, 1 H and 13 C NMR spectroscopies. The crystal structure of 1 has been determined by X-ray crystallography. X-ray analysis revealed a pseudo-pentacoordinated structure containing Ph 3 Sn coordinated to the carboxylato group. The structural distortion is a displacement from the tetrahedron toward the trigonal bipyramid. Significant CÐH±p 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 CÐH±p 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.