The synthesis and structural characterization of a series of triphenyltin(IV) esters of N-arylidene-ω-amino acids

Abstract

. Can. J. Chem. 70, 2683Chem. 70, (1992.Methods of synthesis, elemental analyses, and IR and NMR spectroscopic data are reported for a series of triphenyltin esters of N-salicylidene-w amino acids of the general formula: Ph,SnOCO(CH?),,N=CHAr (Ar = 2-HOC6H4-and 2-HOCloH6-; n = 1, 2, 3, and 5). The crystal structure of triphenyltin N-sajicylidene-6-amin$exanoate was detedmined. The crystals are monoclini:, space group P2,/a, with a = 16.3493 (8) [Traduit par la redaction]

The synthesis, structural characterization and biocidal properties of some triorganotin(IV) esters ofN-arylidene-?-amino acids.

“…8 The melting points and analytical data for the range of carboxylates synthesized are shown in Table 8. Corresponding data for the triphenyltin complexes have been reported previously.…”

“…Corresponding data for the triphenyltin complexes have been reported previously. 8 All the carboxylates listed in Table 8 were isolated as yellow solids that were stable in air. Tributyltin N-salicylideneglycinate was isolated as a liquid which decomposed on distillation under reduced pressure (188-240°C/0.06 mm Hg) and is not included in the table.…”

“…Alternatives to carboxylate bridging for the trans-R 3 SnO 2 structural moiety have been reported, however, for triorganotin carboxylates containing either donor substituent groups 6,7 or a labile phenolic group in the ester function. 8 The relative biocidal activities of these two different structural configurations have not previously been compared.…”

“…Preparation of tributyl-and triphenyl-tin esters of N-arylidene-3 3-amino acids 8 Tributyltin(IV) esters of N-arylidene-3-amino acids were prepared by refluxing in absolute ethanol (ca 90 ml) a mixture of bis(tributyltin) oxide (10 mmol), 3-amino acid (20 mmol) and salicylaldehyde or 2-hydroxynaphthaldehyde (20 mmol). After refluxing for 6-8 h, the reaction mixture was cooled and the product (if there was precipitation) was isolated by filtration; otherwise the reaction mixture was concentrated under reduced pressure before either toluene or petroleum ether (60-80°C) was added to induce precipitation.…”

“…8 A slowly evaporating solution (cyclohaxane, 30 ml) of tributyltin(IV) N-2-hydroxynaphthalidene glycinate (1) (1.6 g) yielded yellow crystals (1.2 g), m.p. 120-121°C, from which a thin yellow plate of dimensions 0.2 mm  0.04 mm  0.04 mm was selected for X-ray analysis.…”