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Diorganotin(IV) complexes of D ‐galacturonic acid: solid‐state and solution‐phase structural study
Author(s) -
Bertazzi N.,
Bruschetta G.,
Casella G.,
Pellerito L.,
Rotondo E.,
Scopelliti M.
Publication year - 2003
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/aoc.556
Subject(s) - chemistry , carboxylate , deprotonation , mössbauer spectroscopy , tin , octahedron , stereochemistry , nuclear magnetic resonance spectroscopy , trigonal bipyramidal molecular geometry , ligand (biochemistry) , medicinal chemistry , crystallography , crystal structure , organic chemistry , ion , biochemistry , receptor
Abstract Three diorganotin(IV) complexes of D ‐galacturonic acid (H 2 GalA; R = Me, n ‐Bu, Ph), two of which are new derivatives (R = Me, Ph), have been synthesized and their solid‐state and solution‐phase investigated by IR, Mössbauer, 1 H, 13 C and 119 Sn NMR spectroscopy. The FTIR data suggest that H 2 GalA, in the dialkyltin derivatives, behaves as a dianionic ligand, coordinating the tin(IV) atom through an ester‐type carboxylate and deprotonated alcoholic hydroxo groups, whereas a bridging carboxylate occurs in the diphenyltin(IV) complex. Octahedral and trigonal bipyramidal local geometries on tin(IV) atoms are proposed for dialkyltin(IV)GalA and diphenyltin(IV)GalA complexes respectively on the basis of Mössbauer spectroscopy. In D 2 O solution, R 2 Sn(IV) moieties seem to be mainly coordinated by the GalA 2− in the β‐furanosidic (β‐GalfA 2− ) form, involving the β‐furanosidic ring in rotational equilibrium. However, the α‐furanosidic (α‐GalfA 2− ), α‐pyranosidic (α‐GalpA 2− ) and the β‐pyranosidic (β‐GalpA 2− ) isomers are also involved in the coordination upon the tin atom to a minor extent. In DMSO‐ d 6 solution, R 2 Sn(IV) moieties are coordinated almost entirely by the GalA 2− in the β‐furanosidic form. Copyright © 2003 John Wiley & Sons, Ltd.