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

  • Farfán N
  • Mancilla T
  • Santillan R
 et al. 
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Abstract

The reaction of salicylaldehyde (1), o-aminophenols (2a-2f), and di-n-butyltinIVoxide (3) to give six di-n-butyltinIVcompounds (4a-4f) was achieved in good yields. All compounds were characterized by1H,13C,15N,119Sn 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 σHammettvs. 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. © 2004 Elsevier B.V. All rights reserved.

Author-supplied keywords

  • Di-n-butyltinIV
  • Multinuclear NMR
  • Schiff base
  • Sigma Hammett
  • X-ray structures

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Authors

  • Teresa Mancilla

  • Rosa Santillan

  • Atilano Gutiérrez

  • Luis S. Zamudio-Rivera

  • Hiram I. Beltrán

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