Catalytically active supramolecular porphyrin boxes: Acceleration of the methanolysis of phosphate triesters via a combination of increased local nucleophilicity and reactant encapsulation

Byungman Kang, Josh W. Kurutz, Kyoung Tae Youm, Ryan K. Totten, Joseph T. Hupp, Sonbinh T. Nguyen

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Box-like tetrakis(metalloporphyrin) supramolecular assemblies possessing Zn and Al metal sites can catalyze the methanolysis of phosphate triesters with a high rate enhancement, up to 430 times faster than the uncatalyzed reaction. Mechanistic studies suggest that the observed rate enhancement can be attributed to a high local concentration of methoxide ion that operates in concert with a solvophobically driven encapsulation of substrates by the porphyrinic assembly.

Original languageEnglish
Pages (from-to)1938-1944
Number of pages7
JournalChemical Science
Volume3
Issue number6
DOIs
Publication statusPublished - Jun 1 2012

ASJC Scopus subject areas

  • Chemistry(all)

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