Journal of Organic Chemistry p. 5958 - 5963 (1989)
Update date:2022-08-17
Topics:
Lacombe, S.
Pellerin, B.
Guillemin, J. C.
Denis, J. M.
Pfister-Guillouzo, G.
Comparison between the electronic structures of N-chloroaldimines and P-chlorophosphaethene has been achieved by photoelectron spectroscopy.Whereas N-chloroaldimines have been synthetized in the gas phase by a new "one-line" reaction starting from α-cyanoamines (vacuum gas-solid reaction, VGSR), P-chlorophosphaethene has been generated by flash vacuum thermolysis (FVT) of dichloromethylphosphine.Chlorine substitution at the heteroatom destabilizes the double bond to a much greater extent for aldimines than for phosphaethene, thus reflecting a greater interaction between chlorine and ?C=N than between chlorine and ?C=P and a more diffuse character of the ?C=P bond than the ?C=N bond.For both series the heteroatom substitution does not modify the ionization energy of the heteroatom lone pair.This observation is evidence for a counterbalance between a stabilizing inductive effect of chlorine and a destabilizing interaction betweeen the lone pairs.The discrepancy between the experimental results and the theoretical evaluation of the ionization potential is again pointed out for compounds bearing third-row atoms involved in double bonds.
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