A green and efficient route for P ? S ? C bond construction using copper ferrite nanoparticles as catalyst: a TD-DFT study
Magnetic nanoparticles of CuFe2O4 were applied as catalyst system for one-pot thiophosphate synthesis via the reaction of aryl sulfonyl chlorides with H-phosphonates under conventional heating conditions. This is an extremely efficient and green method for thiophosphate synthesis under base- and solvent-free conditions. Various thiophosphates were obtained in good to excellent yields under the optimized reaction conditions in a short time. The catalyst can be easily recycled from the reaction by an external magnetic field and reused for the next run. In this study, TD-DFT B3LYP/6-31 + G(d) calculations are in good accord with the experimental results. A comparison between experimental and theoretical UV-vis absorption spectra of the thiophosphate 3k has been carried out; and a small hypsochromic shift (only ~ 2 nm) was displayed at maximum absorption. The aim of this work is to investigate the best method and basis set for thiophosphate compounds; therefore, predictions for these compounds can be performed in theoretical studies.
Reactions of phosphate and phosphorothiolate diesters with nucleophiles: Comparison of transition state structures
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.
Ye, Jing-Dong,Barth, Christofer D.,Anjaneyulu, Potluri S. R.,Tuschl, Thomas,Piccirilli, Joseph A.
p. 2491 - 2497
(2008/02/14)
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