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 language | English (US) |
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Pages (from-to) | 2735-2738 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 7 |
Issue number | 13 |
DOIs | |
State | Published - 2005 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry