STRUCTURAL INVESTIGATION OF 2,6-DI-2-FURYL-3,5-DIMETHYL-4-PIPERIDINONE AND ITS N-NITROSO DERIVATIVE IN SOLUTION AND THE SOLID-STATE INFLUENCE OF THE NITROSO MOIETY ON THE CONFORMATION OF THE PIPERIDINE RING AND ORIENTATION OF ITS SUBSTITUENTS
N. Sukumar et al., STRUCTURAL INVESTIGATION OF 2,6-DI-2-FURYL-3,5-DIMETHYL-4-PIPERIDINONE AND ITS N-NITROSO DERIVATIVE IN SOLUTION AND THE SOLID-STATE INFLUENCE OF THE NITROSO MOIETY ON THE CONFORMATION OF THE PIPERIDINE RING AND ORIENTATION OF ITS SUBSTITUENTS, Bulletin of the Chemical Society of Japan, 67(4), 1994, pp. 1069-1073
The structures of the title compounds, 2,6-di-2-furyl-3,5-dimethyl-4-p
iperidinone (DFMP) and its N-nitroso derivative (DFMPNO), have been in
vestigated in solution and the solid state by NMR and X-ray methods, r
espectively. Both of the structures were solved by direct methods of X
-ray analysis and were refined to an R-factor of 0.059 and 0.057, resp
ectively. The piperidine ring adopts a chair conformation in DFMP and
a boat conformation in DFMPNO. Both of the furan rings are in an equat
orial orientation in DFMP, whereas in DFMPNO one ring is in the axial
position and the other ring is in the equatorial position. The nitroso
group is in the perpendicular orientation in DFMPNO. The angle betwee
n the best plane of the piperidine ring and the nitroso group is 142.1
(4)-degrees. The interaction between the molecules are van der Waals i
n nature in both structures.