Tautomerism in substituted pyridofuroxans: A theoretical study
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Pyridofuroxans present ring-chain tautomerism in analogy with benzofuroxans. In this work we used density functional theory to evaluate the tautomerism in a series of substituted pyridofuroxans and propose a mechanism. The studied substituents are 7-hydroxi, 7-amino, 7-methyl, and 6-bromine; we also studied 4-protonated pyridofuroxan. For all studied pyridofuroxans, calculations suggest three dinitroso intermediate conformers involved in the tautomerism and an energy barrier high enough to avoid tautomerization at room temperature. © 2016 Elsevier B.V..
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B3-LYP; Intramolecular hydrogen bonds; Pyridofuroxans; Tautomerization mechanism
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