Unusual Tautomeric Energetics in 4n Azaheterocycles

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  • Unusual Tautomeric Energetics in 4<i>n</i> Azaheterocycles

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Unusual imino preference in 4n azaheterocycles is theoretically analyzed. It is attributed to less topological charge stability of the amino forms due to antisymmetric nonbonding molecular orbitals. The theory is applicable for designing stable imino species. The same analysis is also applicable for hydroxyl/oxo tautomerism, and results in very stable lactams.

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