Journal of the Chemical Society. Perkin transactions II p. 1851 - 1854 (1984)
Update date:2022-08-04
Topics:
Burke, Padraig O.
McDermott, Sean D.
Hannigan, Thomas J.
Spillane, William J.
36 Di- and mono- and two tri-substituted sulphamides have been synthesised and their ionization equilibria in base (Schemes 1-3) have been studied.Many of the sulphamides are new materials.The pKa values obtained for each series have been correlated in Hammett and Taft plots.The Hammett ? values obtained for the ionization of the proximate hydrogen are ca. 2.3.The Taft ?* value obtained for ionization of the 'remoter' hydrogen is 1.68.The six-membered cyclic sulphamides are more acidic than their acyclic analogues by ca. 2.5 pKa units and the five-membered cyclic sulphamides are ca. 4 pKa units more acidic than model open-chain counterparts.Sulphur d-orbital involvement and ring-strain are suggested as possible sources of this 'acid-strengthening' effect.
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