Solvent effects and mechanism for a nucleophilic aromatic substitution from QM/MM simulations

Orlando Acevedo, William L. Jorgensen

Research output: Contribution to journalArticle

85 Scopus citations

Abstract

(Equation Presented) The nucleophilic aromatic substitution (S NAr) reaction between azide ion and 4-fluoronitrobenzene has been investigated using QM/MM and DFT/PCM calculations in protic and dipolar aprotic solvents. The effects of solvation on the transition structures, the intermediate Meisenheimer complex, and the rate of reaction are elucidated. The large rate increases in proceeding from protic to dipolar aprotic solvents are only reproduced by the QM/MM methodology.

Original languageEnglish (US)
Pages (from-to)2881-2884
Number of pages4
JournalOrganic letters
Volume6
Issue number17
DOIs
StatePublished - Aug 19 2004
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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