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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
Author(s) -
Kamruddin S. K.,
Chattopadhyaya T. K.,
Roy A.,
Tierkink E. R. T.
Publication year - 1996
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/(sici)1099-0739(199609)10:7<513::aid-aoc509>3.0.co;2-v
Subject(s) - chemistry , characterization (materials science) , crystal structure , organic chemistry , stereochemistry , nanotechnology , materials science
The preparation and spectroscopic ( 1 H NMR, UV and IR) characterization of three R 3 Sn(O 2 CCH 2 N(H)C(O)NH 2 ) [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 3 Sn(O 2 CCH 2 N(H)C(O)NH 2 )] 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 symmetry‐related 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 3 SnO 2 motif. The structure of [c‐Hex 3 Sn(O 2 CCH 2 N(H)‐ C(O)NH 2 )], by contrast, is monomeric, distorted tetrahedral, as the carboxylate group is monodentate and there are no additional tin–ligand 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.