79643-60-0Relevant articles and documents
Dipole Moments of Derivatives of 4-Phenylazo-NN-diethylaniline and of 9-Phenylazojulolidine (9-Phenylazo-2,3,6,7-tetrahydro-1H,5H-benzoquinolizine)
Hallas, Geoffrey,Saadatjou, Naghi,Hepworth, John D.,Ibbitson, Douglas A.,Jones, Alan M.,et al.
, p. 1292 - 1294 (2007/10/02)
Apparent dipole moments in benzene of a series of para-substituted derivatives of 9-phenylazojulolidine (9-phenylazo-2,3,6,7-tetrahydro-1H,5H-benzoquinolizine) have been determined together with those of the corresponding series derived from 4-phenylazo-NN-diethylaniline.Vector moments, μ(int), in the direction of the major axis of the molecules have been calculated in order to explain the observed moments.The values of μ(int) for the 9-phenylazojulolidines are all greater than those for the corresponding 4-phenylazo-NN-diethylanilines and, for both series of compounds, increase with increase in the Hammett substituent parameter, ?p.Evidence is presented that the terminal nitrogen atom is more nearly planar in the 9-phenylazojulolidines than in the 4-phenylazo-NN-diethylanilines and also that μ(int) arises by interaction of the para-substituent with the ?-electron distribution in the aromatic ring to which it is attached.
