35337-68-9Relevant articles and documents
Reactions of phosphate and phosphorothiolate diesters with nucleophiles: Comparison of transition state structures
Ye, Jing-Dong,Barth, Christofer D.,Anjaneyulu, Potluri S. R.,Tuschl, Thomas,Piccirilli, Joseph A.
, p. 2491 - 2497 (2008/02/14)
A series of methyl aryl phosphorothiolate esters (SP) were synthesized and their reactions with pyridine derivatives were compared to those for methyl aryl phosphate esters (OP). Results show that SP esters react with pyridine nucleophiles via a concerted SN2(P) mechanism. Bronsted analysis suggests that reactions of both SP and OP esters proceed via transition states with dissociative character. The overall similarity of the transition state structures supports the use of phosphorothiolates as substrate analogues to probe mechanisms of enzyme-catalyzed phosphoryl transfer reactions. This journal is The Royal Society of Chemistry.
Kinetics of the Reactions of 2,4-Dinitrophenyl Aryl Sulphides Sulphoxides and Sulphones with Hydroxide Ion in 80 percent (v/v) Ethanol-Water
Hamed, E. A.,El-Bardan, A. A.,Saad, Esmat F.,Fathalla, Magda F.
, p. 177 - 186 (2007/10/03)
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The E1cB Mechanism for Thiocarbamate Ester Hydrolysis: Equilibrium and Kinetic Studies
Bourne, Nicholas,Williams, Andrew,Douglas, Kenneth T.,Penkava, Thomas R.
, p. 1827 - 1832 (2007/10/02)
The alkaline hydrolyses of a series of S-aryl thiocarbamate esters have been measured and the mechanism confirmed to be dissociative.Equilibrium constant for the synthesis of thiocarbamates from thiol and isocyanic acid have been obtained for aqueous media using both kinetic and analytical techniques.Hammett and Broensted parameters for the equilibrium reaction indicate that there is less positive effective charge on the sulphur in the thiocarbamate compared with that on the oxygen in the oxygen analogue.Theoretical arguments are advanced to show that the dissociative reactions of simple carbamate anions involve a planar geometry of the paticipating atoms.