Electronic properties of the nitrosamine function

The addition of a chiral alcohol, such as l-menthol or R-(-)-2-octanol, to an achiral nitrosamine causes a dissymmetric perturbation of the symmetrical chromophore and a Cotton effect is evident in the circular dichroism curve at the wavelength of ultraviolet absorption of the nitrosamine function. The intensity (ellipticity) of this induced circular dichroism is concentration dependent and appears to result from a weak 1:1 complex of nitrosamine and alcohol. The implications of these observations for structural studies are considered.