109879-22-3Relevant academic research and scientific papers
CONFORMATIONAL AND PROTOTROPIC ISOMERISM IN THE PRODUCTS FROM N-ACYLATION OF 2-DIMETHYLAMINOMETHYLCYCLOHEXANONE BENZYLIMINE
Kayukova, L. A.,Dyusenova, Z. M.,Erzhanov, K. B.
, p. 1662 - 1668 (2007/10/02)
The slow rotation about N-Csp2 and N-Csp2=O single bonds in the two isomeric enamine forms of the products from the N-acylation of 2-dimethylaminomethylcyclohexanone benzylimine with a trisubstituted (A) and a tetrasubstituted (B) C=C double bond in the cyclohexene ring was studied by (1)H NMDR.The predominating conformer of the enamine form A is the exo conformer, which has N-Csp2 rotation barriers of 49.4-59.0 kJ/mole in the series of investigated compounds; the predominating isomer of the enamine form B is the endo isomer with a N-Csp2 rotation barrier of more than 93 kJ/mole.The prototropic equilibrium A B is characterized by positive changes of the thermodynamic parameters ( ΔG0298, ΔH0, ΔS0) in carbon tetrachloride and nitrobenzene, and this corresponds to greater stability for the enamine form A.
