Preference of di-n-butyltinIV compounds to build O⋯Sn bonds in fused rings with five-six members

Abstract The reaction of salicylaldehyde ( 1 ), o -aminophenols ( 2a – 2f ), and di- n -butyltin IV oxide ( 3 ) to give six di- n -butyltin IV compounds ( 4a – 4f ) was achieved in good yields. All compounds were characterized by 1 H, 13 C, 15 N, 119 Sn NMR, mass spectrometry, IR, elemental analysis and in the case of compounds 4a , 4b , 4d and 4e by X-ray diffraction analysis. Compound 4a crystallized with trigonal bipiramidal (TPB) geometry surrounding the tin atom while 4b and 4e crystallized as dimeric molecules joined by two O⋯Sn bonds with distorted octahedron (DOC) geometry. The X-ray structure of 4d presents one cocrystallized monomeric TBP with one dimeric DOC molecule. Correlations of σ Hammett vs. spectroscopic values were found for 4a – 4b and 4d – 4f , indicating the substituents in the aromatic ring derived from o -aminophenol serve as modulators of the O⋯Sn supramolecular interaction. The O⋯Sn bond formation is selective for the five-membered ring oxygen atom.