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Cu(II)‐catalyzed hydrolysis of tris‐2‐pyridyl phosphate assisted by sodium dodecyl sulfate micelles
Author(s) -
Wanderlind Eduardo H.,
Bittencourt Catiunaiara R.,
Manfredi Alex M.,
Gerola Adriana P.,
Souza Bruno S.,
Fiedler Haidi D.,
Nome Faruk
Publication year - 2019
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3837
Subject(s) - chemistry , micelle , tris , hydrolysis , sodium dodecyl sulfate , phosphate , inorganic chemistry , catalysis , substrate (aquarium) , nanoreactor , ligand (biochemistry) , intramolecular force , organic chemistry , aqueous solution , biochemistry , oceanography , receptor , geology
Hydrolysis of the phosphate triester tris‐2‐pyridyl phosphate is catalyzed upon complexation with Cu 2+ , with enhancements of the order of 10 7 ‐fold in comparison to the spontaneous hydrolysis of the substrate. Experimental and theoretical results suggest that Cu 2+ most probably coordinates to the nitrogen atoms of two of the pyridyl substituents disposing a metallo‐bound water or hydroxo ligand at appropriate distance for intramolecular attack on phosphorus. Micelles of the anionic sodium dodecyl sulfate remarkably accelerate the reactions, acting as nanoreactors that concentrate in the micellar microenvironment both the hydrophobic substrate and the positively charged metal ion, favoring complexation between tris‐2‐pyridyl phosphate and Cu 2+ .