Conformational studies on chloramphenicol and related molecules

A conformational analysis has been performed on chloramphenicol and related molecules by potential energy functions, NMR and IR spectroscopy. Specific solvent effects have been considered via calculation in the case of chloramphenicol. The results establish that essentially only one conformer of chloramphenicol exists in solution with respect to the C_αC_β bond, but that this stabilization is not due to hydrogen bonding as proposed in a previous study. The importance of stabilization of polar solute conformations in polar media is also discussed.