Collect. Czech. Chem. Commun. 1997, 62, 279-298

Synthesis and Infrared and 1H, 13C, 119Sn NMR Spectra of Some Tris- and Bis(1-butyl)tin(IV) Naphthoates and Hydroxynaphthoates

Jaroslav Holečeka, Milan Nádvorníka, Karel Handlířa, Vladimír Pejchala, Radovan Víteka and Antonín Lyčkab

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


The synthesis and structure of tris(1-butyl)tin(IV) and bis(1-butyl)tin(IV) 1-naphthoates, 2-naphthoates, 1-hydroxy-2-naphthoates, 2-hydroxy-1-naphthoates, 3-hydroxy-2-naphthoates as well as the groups of the corresponding tetrakis(1-butyl)dinaphthoato- and tetrakis(1-butyl)bis(hydroxynaphthoato)distannoxanes have been studied in solutions of both coordinating and noncoordinating solvents by means of infrared and multinuclear (1H, 13C and 119Sn) NMR spectroscopies. In the solutions of noncoordinating solvents, all the tris(1-butyl)tin(IV) compounds are present as isolated monomeric molecules with pseudotetrahedral environment of the central tin atom, or as strongly deformed cis-trigonally bipyramidal chelate complexes with anisobidentate carboxylic group. The bis(1-butyl)tin(IV) compounds form molecular pseudooctahedral complexes with chelate anisobidentate carboxylic groups of naphthoate or hydroxynaphthoate ligands. The (1-butyl)chlorotin(IV) compounds are molecular complexes containing a chelate-bound carboxylic group, their tin atom having a pentacoordinated environment of the bond partners. The tetrakis(1-butyl)dinaphthoato- and tetrakis(1-butyl)bis(hydroxynaphthoato)distannoxanes form dimeric molecular complexes with two pentacoordinated tin atoms and two hexacoordinated ones. In solutions of a coordinating solvent (hexadeuteriodimethyl sulfoxide), the tris(1-butyl)tin(IV) compounds form trans-trigonally bipyramidal complexes with one molecule of the solvent, whereas the bis(1-butyl)tin(IV) and bis(1-butyl)chlorotin(IV) compounds form trapezoidally bipyramidal complexes with two molecules of the solvent. The dimeric tetrakis(1-butyl)bis(hydroxynaphthoato)distannoxanes are monomerized by coordinating solvent, each monomeric unit adding two solvent molecules per one tin atom. The environment of the tin atom is then pseudooctahedral. The hydroxyl groups of naphthoate systems do not take part in any bonds to the tin atom in any of the compounds studied.

Keywords: Tris(1-butyl)tin(IV) naphthoates and hydroxynaphthoates; Bis(1-butyl)tin(IV) dinaphthoates and bis(hydroxynaphthoates); Structure; 1H, 13C, 119Sn NMR spectroscopy; Infrared spectroscopy.