2514-19-4Relevant academic research and scientific papers
IMINATION OF SULFUR-CONTAINING COMPOUNDS. XXIV. EFFECT OF THE ACIDIC CHARACTERISTICS OF THIOLS ON THE IMINATION OF SODIUM THIOLATES BY DICHLOROSULFONAMIDES
Koval', I. V.,Tarasenko, A. I.,Kremlev, M. M.
, p. 362 - 367 (2007/10/02)
The ability of sodium thiolates to be iminated by dichlorosulfonamides is due to a series of factors and primarily to the acidic characteristics of the initial thiols.The sodium salts of thiols with pKa > 8 are iminated comparatively readily by dichlorosulfonamides.Decrease in the pKa values of the thiols to 5-7 leads to a decrease in the imination rate and in the yields of the respective N,N'-bis(arylsulfonyl)sulfinamidines.The sodium salts of thiols with pKa 5 are not iminated by dichlorosulfonamides.Investigation of the acidic characteristics of the N,N'-bis(arylsulfonyl)sulfinamidines showed that substituents in the sulfinamidine fragment of the molecule make a larger contribution to the change in the acidic characteristics of the compounds than substituents in the arenesulfonyl fragment.
IMINATION OF SULFUR-CONTAINING COMPOUNDS. XXIII. EFFECT OF THE ACIDIC CHARACTERISTICS OF N-SUBSTITUTED SULFENAMIDES ON THEIR ABILITY TO BE IMINATED BY THE SODIOCHLOROAMIDES OF SULFONIC ACIDS
Koval', I. V.,Oleinik, T. G.,Tarasenko, A. I.,Kremlev, M. M.
, p. 2358 - 2365 (2007/10/02)
The ability of N-substituted sulfenamides to be iminated by the sodiochloroamides of sulfonic acids is due primarily to their acidity and to the type of solvent employed.N-Substituted sulfonamides with pKa > 11.0 are imidated by the sodiochloroamides of sulfonic acids in acetone.The imination of N-substituted sulfenamides with pKa 8-11 must be carried out in strongly basic solvents with high dielectric constants (an aqueous alkaline medium, pyridine, etc.); sulfenamides with pKa 8 are iminated by the sodiochloroamides of sulfonic acids in the form of the sulfenamide anion.
