Homolytic C-alpha-C-beta bond cleavage in a chiral alkylarene radical cation: Effects of asymmetric microsolvation

Fragmentation of the (R)-(+)-1-phenyl-1-propanol radical cation ([(BZC 2H5)R]+) is markedly affected by asymmetric microsolvation (see picture). The C?-C ? bond cleavage in the heterochiral [ (BZC2H 5)R.BDSS]+ cluster is more efficient than in the homochiral [(BZC2H5) R.BDRR]+. The difference is ascribed to structural factors that make BDSS a better H-bond acceptor than BDRR in their adducts with [(BZC2H5) R]+. BZ = PhCHOH, BD = 2,3-butanediol.