45797-13-5Relevant articles and documents
Identification of dimethyl sulfide in dimethyl sulfoxide and implications for metal-thiolate disulfide exchange reactions
Garusinghe, Gamage S. P.,Bessey, S. Max,Boyd, Chelsea,Aghamoosa, Mostapha,Frederick, Brian G.,Bruce, Mitchell R. M.,Bruce, Alice E.
, p. 40603 - 40606 (2015)
The concentration of dimethyl sulfide (DMS) in seven different samples of research grade dimethyl sulfoxide (DMSO), including one deuterated sample, was measured by GC-MS. The average concentration of DMS is 0.48 ± 0.14 mM (range: 0.44-0.55 mM) and ca. 0.
Kinetics and mechanism of the reactions of O-aryl S-(4-nitrophenyl) dithiocarbonates with anilines in aqueous ethanol
Castro, Enrique A.,Gazitua, Marcela,Santos, Jose G.
scheme or table, p. 176 - 180 (2010/08/20)
The reactions of O-(4-methylphenyl) S-(4-nitrophenyl) dithiocarbonate and O-(4-chlorophenyl) S-(4-nitrophenyl) dithiocarbonate with a series of anilines are subjected to a kinetic investigation in 44wt% ethanol-water, at 25.0 °C and an ionic strength of 0.2 M. The reactions are followed spectrophotometrically at 420nm (appearance of 4-nitrobenzenethiolate anion). Under excess amine, pseudo-first-order rate coefficients (kobs) are found. For the reactions of both substrates with anilines, plots of k obs versus free amine concentration at constant pH are nonlinear upwards, according to a second-order polynomial equation. This kinetic behavior is in agreement with a stepwise mechanism consisting of two tetrahedral intermediates, one zwitterionic (T±) and the other anionic (T-), with a kinetically significant proton transfer from T ± to an aniline to yield T-. The rate equation was derived from the proposed mechanism. By nonlinear least-squares fitting of the rate equation to the experimental data, values of the rate micro-coefficients involved in both steps were determined. Copyright
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.
