82360-60-9Relevant academic research and scientific papers
CONFIGURATION AND CONFORMATION OF AMIDOXIMES. N,N-DIALKYL DERIVATIVES
Exner, Otto,Motekov, Nedelko
, p. 814 - 827 (2007/10/02)
Dipole moments of N,N-dialkylamidoximes Ia-Ie and of substituted O-benzoyl-N,N-dimethylbenzamidoximes IIa-IIe were measured in benzene or dioxan, respectively.The results with the later set of compounds allow to assign in an independent and unambiguous way the E-configuration which was found previously for all N,N-dialkylamidoximes investigated in the crystalline state; our reasoning does not involve bond moment values within the amidoxime functional group.The fundamental difference in the stereochemistry between unsubstituted amidoximes and their N,N-dialkyl derivatives has been confirmed.On the other hand, the configuration of simple N,N-dialkylamidoximes (e.g.Ia-Ie) cannot be deduced from their dipole moments in a straightforward manner.The reason is that the conjugation within the N=C-N chain requires a mesomeric correction term which cannot be neglected and is not equal in either configuration.The example shows very clearly limitations of the bond moment approach if applied to conjugated molecules.
