Manifestation of stereoelectronic effects on the calculated carbon–nucleophile bond lengths in nucleophilic addition to sterically unbiased ketones

Calculations at the B3LYP/6-311G(d,p) level of the structures of diastereoisomeric pairs of alcohols 1E–12E and 1Z–12Z, resulting from either reduction or methylation of sterically unbiased ketones show that the newly formed C–Nu bond lengths of the major isomers are larger than those of the minor isomers.