Optically Active Amines. Part XIII. Circular Dichroism of the N-Salicylidene Derivatives of Alkylamines
Comparison of the c.d. spectra of (S)-(+)-N-salicylidene-α-phenylethylamine with those of (S)-(+)-N-salicylidene-sec-butylamine and (R)-(−)-N-salicylidene-2,2-dimethyl-3-aminobutane confirms the conclusion that the strong rotational strength shown by N-salicylidene-α- and β-phenylalkylamines is due to an interaction of the π-electron System of the phenyl group and the salicylidenimino chromophore. The sign of the Cotton effects near 255 and 315 nm shown by the N-salicylidenes of alkylamines and cycloalkylamines, when these are conformationally defined, can be correlated with their absolute configurations using a planar sector rule, similar to that used for the interpretation of the c.d. and o.r.d. spectra of N-salicylidene-α- and β-phenylalkylamines.