Probing Stereoelectronic Interactions in an O–N–OUnit by the Atomic Energies: Experimental and Theoretical ElectronDensity Study.

Stereoelectronic interaction lp(O1)→ σ*(N1–O2)in a O–N–O unit was analyzed by means of R. Bader’sAtoms in Molecule theory on the basis of X-ray diffraction data fordimethyl-(2R,4aR,5S,7R)-2,5,7-triphenylhexahydro-4H-[1,2]oxazino[2,3-b][1,2]oxazine-4,4-dicarboxylate. Atomic energiesobtained by applying this approach to both the experimental and theoreticalelectron densities were used to probe the energy of this strong stereoelectronicinteraction, giving consistent results with the NBO analysis, althoughshowing its destabilizing character. [ABSTRACT FROM AUTHOR]