Details

Autor(en) / Beteiligte

• Wanderlind, Eduardo H.
• Bittencourt, Catiunaiara R.
• Manfredi, Alex M.
• Gerola, Adriana P.
• Souza, Bruno S.
• Fiedler, Haidi D.
• Nome, Faruk

Titel

Cu(II)‐catalyzed hydrolysis of tris‐2‐pyridyl phosphate assisted by sodium dodecyl sulfate micelles

Ist Teil von

• Journal of physical organic chemistry, 2019-01, Vol.32 (1), p.n/a

Ort / Verlag

Bognor Regis: Wiley Subscription Services, Inc

Erscheinungsjahr

2019

Quelle

Wiley Online Library - AutoHoldings Journals

Beschreibungen/Notizen

• Hydrolysis of the phosphate triester tris‐2‐pyridyl phosphate is catalyzed upon complexation with Cu2+, with enhancements of the order of 107‐fold in comparison to the spontaneous hydrolysis of the substrate. Experimental and theoretical results suggest that Cu2+ 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 Cu2+. Complexation between Cu2+ and tris‐2‐pyridyl phosphate catalyzes the phosphate hydrolysis, most probably trough intramolecular nucleophilic attack of a water ligand on phosphorus. Micelles of sodium dodecyl sulfate favor the reaction, allowing for high local concentrations of Cu2+ in the micellar environment.