M. Blanc-Muesser, J. Defaye, D. Hopton
Feb 1, 1979
Citations
0
Influential Citations
16
Citations
Journal
Carbohydrate Research
Abstract
Abstract The conformations of the four 1-amino-1-deoxy- D -pentitols and their hydrochlorides in deuterium oxide solution have been analyzed by 250-MHz, 1 H-n.m.r. spectroscopy. The data indicate that the D - arabino ( 2 ) and D - lyxo ( 3 ) isomers adopt extended, planar, zigzag conformations, whereas the D - xylo ( 4 ) and D - ribo ( 1 ) isomers have the carbon chain in a nonplanar, “sickle” arrangement. The conformational assignments parallel closely those previously advanced for various related series of acetylated derivatives in organic solvents, and for nonacetylated analogs in solution and in the crystalline state. The spectral changes that take place in solution upon converting the amines 1–4 into their amine-salt forms are discussed, and the conformational data are considered in relation to the reactivity of 1–4 on deamination with nitrous acid and with respect to related reactions leading to ring closure under kinetic conditions.