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N-di- and tri-organotin(IV) derivatives of saccharin

1984; Elsevier BV; Volume: 266; Issue: 3 Linguagem: Inglês

10.1016/0022-328x(84)80135-7

1872-8561

F. A. K. Nasser, J. J. Zuckerman,

Synthesis and Reactivity of Sulfur-Containing Compounds

Eleven N-di- and tri-organotin(IV) derivatives of saccharin, RnSn[NC(O)C6H4SO2]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−), ν(SO2) (1375–1115 cm−), ν(SnC) (600–500 cm−) and ν(SnNCO) (380–349 cm−). 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 triphenyltin(IV) derivative is the parent molecular ion seen. The tin-119m Mossbauer 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°. The N-triorganotin(IV) derivatives have equatorial R3Sn groups which are approximately planar.