Geminal Bis(haloorganostannanes) and Their Complexation as Mono- and Bidentate Lewis Acids with Dimethyl Sulfoxide

Thomas J. Karol, John P. Hutchinson, Jeffrey R. Hyde, Henry G. Kuivila, Jon A. Zubieta

Research output: Contribution to journalArticlepeer-review

62 Scopus citations


Six (chloromethylstannyl)methanes with structures CH2(SnMenCl3_n)(SnMemCl3-m) with n = 0-3 and m = 0-2 have been prepared by chlorine-methyl exchange from bis(trimethylstannyl)methane or bis-(trivinylstannyl)methane. Four 2,2-bis(chloromethylstannyl)propanes have been similarly prepared from 2,2-bis(trimethylstannyl)propane. Correlations between 1H and 13C magnetic resonance parameters have been examined. The effects of dimethyl sulfoxide (Me2SO) on the 1H NMR parameters of the chloro-stannanes have been examined as a source of information on complexation. Seven complexes with Me2SO have been prepared, and the structures of CH2(SnMeCl2)-(SnMe2Cl)(Me5SO)λ4, CH2(SnMeCl2)2(2Me2SO)λ5, and CH2(SnCl3)2(4Me2SO)λ7 have been determined by X-ray diffraction. In the first of these, the oxygen of the Me2SO bridges the two tins which display distorted trigonal-bipyramidal geometry; in the second, the oxygens of each Me2SO act as bridges between the tins which display distorted octahedral geometry; in the third, the oxygens do not bridge and the CH2 group serves as a common apex for the octehedra of two hexacoordinate tins. Pertinent features of the structures are discussed. Compound 4 crystallizes in the space group P1 with a = 7.551 (2) A, b = 7.945 (2) A, c = 13.354 (3) A, a = 80.63 (2), β = 89.13 (2), 7 = 72.96 (2), and Z = 2. The structure solution and refinement were based on 1609 reflections with F0 > 6σ(F0) to give a discrepancy factor of 0.045. Compound 5 crystallizes in the orthorhombic space group Pbnm with a = 9.821 (2) A, b = 12.411 (2) A, c = 15.540 (3), and Z = 4. Refinement based on 1109 reflections with Fo > 6σ(Fo) converged at 0.048. Compound 7 crystallizes in the monoclinic space group C2/c with a = 20.998 (5) A, b = 7.925 (3) A, c = 16.535 (4), β = 98.79 (3), and Z = 4. Refinement using 1277 reflections with Fo > 6σ(Fo) yielded R = 0.034.

Original languageEnglish (US)
Pages (from-to)106-114
Number of pages9
Issue number1
StatePublished - Jan 1983
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry


Dive into the research topics of 'Geminal Bis(haloorganostannanes) and Their Complexation as Mono- and Bidentate Lewis Acids with Dimethyl Sulfoxide'. Together they form a unique fingerprint.

Cite this