(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).
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry