13C CHEMICAL SHIFTS AND CARBONYL STRETCHING FREQUENCIES AS STRUCTURAL PROBES FOR FERROCENYL KETONES

Article abstract of DOI:10.1016/S0022-328X(00)99480-4

13C chemical shifts (δ(CO)) have been measured for a series of aromatic ferrocenyl ketones (FcCOC6H4X) and some sterically hindered analogues (FcCOR, R=mesityl, anthracyl, t-Bu, adamantyl).The shifts correlated quite well with those of the corresponding benzophenones.From the carbonyl carbon shifts (δ(CO)), estimates were made of the interplanar angle between the carbonyl sp² and the phenyl ring planes.Substituent effects of the Cp ring carbons are discussed.The solution (CCl4) infrared spectra of the derivatives were obtained and the carbonyl stretching frequency (ν(CO)) was found to correlate roughly with δ(CO).Estimates were also made of the interplanar angle between the cyclopentadienyl ring plane and the carbonyl plane, for sterically hindered ketones using δ(CO) values.