N-DI AND TRI-ORGANOTIN(IV) DERIVATIVES OF SACCHARIN

Article abstract of DOI:10.1016/0022-328X(84)80135-7

Eleven N-di and tri-organotin(IV) derivatives of saccharin, RnSn(4-n), where n = 2, R = CH3, C2H5, n-C4H9, C6H5, n-C8H17 and where n = 3, R = CH3, C2H5, n-C3H7, n-C4H9, C6H5, c-C6H11 are synthesized in high yield by reaction of the corresponding organotin(IV) chlorides with the ammonium salt of saccharin in methanol.The products are colorless crystals, soluble in organic solvents.Vibrational spectroscopic band assignments are made for the ν(CO) (1710-1590 cm^-1), ν(SO2) (1375-1115 cm^-1), ν(Sn-C) (600-500 cm^-1) and ν(Sn-NCO) (380-349 cm^-1).No fragments of mass greater than the parent molecular ion or containing more than one tin atom are seen in the mass spectra at 12 eV of any of the compounds studied.Only in the triophenyltin(IV) derivative is the parent molecular ion seen.The tin-119m Moessbauer isomer shift (IS) values confirm tin as tin(IV), and the quadrupole splitting (QS) and ρ(QS/IS), values are typical of higher than four-coordination with the NMR<*>²J(119Sn-C-1H)<*> coupling constants of the methyltins in solution corroboratory.From the QS values of the N-diorganotin(IV) derivatives a point charge model is used to calculate the carbon-tin-carbon angles.The magnitudes of these angles suggest that these derivatives have a generally trans-R2Sn configuration with predicted angles in the range 139-180 deg.The N-triorganotin(IV) derivatives have equatorial R3Sn groups which are approximately planar.