Mechanism and Catalysis of Nucleophilic Substitution in Phosphate Esters

R. J.Gregory Thatcher, Ronald Kluger

Research output: Contribution to journalArticlepeer-review

364 Scopus citations


The chapter discusses the various mechanism and catalysis of nucleophilic substitution in phosphate esters. The mechanism of substitution reactions of phosphate esters and related compounds has been the subject of many significant recent investigations. The reason for this interest can be traced to the biochemical significance of phosphate esters and their applications. These materials are utilized in metabolism and genetic processes, and energy is released upon their hydrolysis. Yet in the absence of enzymes, they appear almost inert. The means by which their reactivity is enhanced by an enzyme continues to be a challenging problem for mechanistic investigation. This challenge requires, as a background, an assured knowledge of the reaction mechanisms of these materials in the absence of enzymes and the means by which catalysis can be achieved. Various investigations involving kinetics, stereochemistry, isotope effects, magnetic resonance, theory, and other techniques have been dealt with in this area.

Original languageEnglish (US)
Pages (from-to)99-265
Number of pages167
JournalAdvances in Physical Organic Chemistry
Issue numberC
StatePublished - Jan 1 1989
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry


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