Interactive n→σ* delocalizations that control an aqueous organic equilibrium

Article abstract of DOI:10.1016/S0040-4039(97)82941-3

Hydrated acetaldehydes were condensed in D₂O with substituted alcohols and thiols to determine ΔG of hemiacetalization by ¹H NMR. Specific n→σ* delocalizalions in the alkoxy/alkylthio functionality of the product interact to influence n→σ* delocalization in the hemiacetal functionality. Delocalization in the latter functionality controls ΔG.