Model studies of the histidine-tyrosine cross-link in cytochrome c oxidase reveal the flexible substituent effect of the imidazole moiety

Derek A. Pratt, Russell P. Pesavento, Wilfred A. Van Der Donk

Research output: Contribution to journalArticlepeer-review

Abstract

(Chemical Equation Presented) Experimental and theoretical studies were carried out to interrogate the effect of an imidazole substituent in each of the ortho, meta, and para positions on the pKa, E°, and O-H BDE of phenol. The results reveal that imidazole substitution lowers the pKa of phenol and increases the E° of phenoxide due to its σ-electron withdrawing ability (σp- = +0.21, σm- = +0.45) but decreases the O-H BDE and E° of phenol due to its π-electron-donating ability (σp + = -0.45).

Original languageEnglish (US)
Pages (from-to)2735-2738
Number of pages4
JournalOrganic Letters
Volume7
Issue number13
DOIs
StatePublished - 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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