Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry and Computational Chemistry


On the electrophilic reactivities of a-carbonyl heterocylces and arenes

Author(s): Jeffrey L. Wells, Douglas A. Klumpp

A series of heterocyclic aldehydes and substituted benzaldehydes were studied for their tendencies to form hemiacetal products with methanol. The equilibrium ratios were compared with DFT calculated molecular orbital levels and the hemi-acetal content was found to correlate roughly to the energy level of the lowest unoccupied molecular orbitals (LUMOs). Hemi-acetal formation is enhanced by intramolecular hydrogen bonds and diminished by steric effects.

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