Collect. Czech. Chem. Commun. 1997, 62, 1169-1176

119Sn, 13C and 1H NMR Spectra of Tris(1-butyl)stannyl D-Glucuronate

Antonín Lyčkaa, Jaroslav Holečekb and David Micákb

a Research Institute of Organic Syntheses, 532 18 Pardubice-Rybitví, Czech Republic
b Department of General and Inorganic Chemistry, Faculty of Chemical Technology,University of Pardubice, 532 10 Pardubice, Czech Republic


The 119Sn, 13C and 1H NMR spectra of tris(1-butyl)stannyl D-glucuronate have been measured in hexadeuteriodimethyl sulfoxide, tetradeuteriomethanol and deuteriochloroform. The chemical shift values have been assigned unambiguously with the help of H,H-COSY, TOCSY, H,C-COSY and 1H-13C HMQC-RELAY. From the analysis of parameters of 119Sn, 13C and 1H NMR spectra of the title compound and their comparison with the corresponding spectra of tris(1-butyl)stannyl acetate and other carboxylates it follows that in solutions of non-coordinating solvents (deuteriochloroform) the title compound is present in the form of more or less isolated individual molecules with pseudotetrahedral environment around the central tin atom and with monodentately bound carboxylic group. The interaction of tin atom with oxygen atoms of carbonyl group and hydroxyl groups of the saccharide residue - if they are present at all - are very weak. In solutions in coordinating solvents (hexadeuteriodimethyl sulfoxide or tetradeuteriomethanol), the title compound forms complexes with one molecule of the solvent. Particles of these complexes have a shape of trigonal bipyramid with the 1-butyl substituents in equatorial plane and the oxygen atoms of monodentate carboxylic group and coordinating solvent in axial positions.

Keywords: Tris(1-butyl)stannyl D-glucuronate; 119Sn, 13C and 1H NMR.