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Biocidal Organotin Compounds. Part 2. Synthesis, Characterization and Biocidal Properties of Triorganotin(IV) Hydantoic Acid Derivatives and the Crystal Structures of Triphenyltin and Tricyclohexyltin Hydantoates

✍ Scribed by S. K. Kamruddin; T. K. Chattopadhyaya; A. Roy; E. R. T. Tierkink

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 651 KB
Volume: 10
Category: Article
ISSN: 0268-2605
DOI: 10.1002/(sici)1099-0739(199609)10:7<513::aid-aoc509>3.0.co;2-v

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✦ Synopsis

The preparation and spectroscopic ('H NMR, UV and IR) characterization of three R,Sn(O,CCH,N(H)C(O)NH,) [R=Ph, c-Hex (cyclohexyl) or n-Bu] compounds are reported. A different mode of coordination is indicated for the hydantoate ligand in the R=Ph compound compared with the R=c-Hex and R=n-Bu compounds, as confirmed by a crystallographic analysis. The structure of [ Ph,Sn (0,C C H,N(H) C( O)NH, )I is polymeric owing to the presence of bridging hydantoate ligands such that each ligand coordinates one tin atom, via one of the carboxylate oxygen atoms, and a symmetryrelated tin atom via the carbonyl group at the other end of the molecule. The structure features distorted trigonal-bipyramidal tin atom geometries with a trans-R,SnO, motif. The structure of [c-Hex,Sn(O,CCH,N(H)-C(O)NH,)], by contrast, is monomeric, distorted tetrahedral, as the carboxylate group is monodentate and there are no additional tinligand interactions. The structures are each stabilized by a number of intermolecular hydrogen bonds. Fungitoxicity and phytotoxicity studies indicate that the R=n-Bu derivative is the more active compound.

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