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Basicity of S(IV)N(sp2)S(VI) group in N-sulphonyl sulphilimines

✍ Scribed by I. Kapovits; F. Ruff; Á. Kucsman

Publisher
Elsevier Science
Year
1972
Tongue
French
Weight
350 KB
Volume
28
Category
Article
ISSN
0040-4020

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✦ Synopsis

The extent of protonation of several N-sulphonyl sulphilimines of XC,H,(Me)SNTs and MePhSNSO,C,H,Y type has been measured in aqueous sulphuric acid by the UV technique. Sulphilimines follow the H, acidity function and thermodynamic pK.'s can be calculated from the equation given for Hammett-bases. The pK.'s range from -1.81 (X = p-OMe) to -400 (Y = p-NO,). Structural effects on the basicity of the SNS group are similar to those of the SO group in sulphoxides The Hammett p values for substituted sulphilimines are p x = +089 and pv = +082 The basicities ofsulphilimines are discussed and compared to those of nitrogen(sp') bases and other sulphur compounds.

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Ab initio molecular orbital (MO) calculations for two series of sulfur-oxygen compounds are reported: the S(IV) system of SOa, H2S03, HSO,, and SO:-, and the S(VI) system of so3, H2S04, HSO;, and SO:-. Geometries about the sulfur atoms were optimized using the STO-3G\* basis set; energies at these g