Chem & Physics Quiz
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A resonance comparison was performed on diazines to rationalize substitution patterns in a medicinal scaffold. The central concept is electron withdrawal and EAS deactivation in multiple-nitrogen heteroarenes. Consider pyridine (one ring N) versus pyrimidine (1,3-diazine; two ring nitrogens). Each ring N is pyridine-like (its lone pair is not part of the aromatic sextet) and withdraws electron density by induction and resonance.
Under identical EAS nitration conditions, which ring is expected to be more strongly deactivated toward electrophilic substitution?
(Structures: pyridine = C5H5N; pyrimidine = C4H4N2 with N at positions 1 and 3.)
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