文摘
A systematic analysis of the conformation of the sulfonamide bond at various levels of ab initio MO theory shows distinct differences in comparison to the amide/peptide bond. Most important are (i) the different values of the torsion angle ω (∠CαSNCα), which are about −100 and 60° in the two basic conformers of the sulfonamide bond, but about 180 and 0° for the peptide bond, (ii) the rotation barriers around the SN bond, which are distinctly lower than for the peptide bond, thus making sulfonamido peptides more flexible, and (iii) the pyramidal nature of the sulfonamide nitrogen in the conformers in comparison to a practically planar arrangement of the peptide bond.