Stereochemical Elucidation of Aldoses from the 1H NMR Spectrum of Its Peracetylated Aldononitrile Derivatives with the Aid of MM2/3JHH Calculations

The root mean square criterion is applied to compare the calculated and experimental H,H vicinal coupling constants of the peracetylated aldononitriles (PAAN) derived from threose, all the pentoses, all of the hexoses, and one heptose. The correlation is satisfactory in all the studied cases. This result supports the possibility of a complete stereochemical elucidation of an aldose from the NMR spectrum of its PAAN derivative. © 1990, American Chemical Society. All rights reserved.