Asymmetric unbridged nitrogen. 39. configurations and conformations of N-substituted perhydro-1,3,2 -dioxazines -
The stereochemical peculiarities of N-substituted perhydro-1,3,2-dioxazines were analyzed thoroughly on the basis of NMR spectroscopic data, the results of x-ray diffraction analysis, and quantitative MO theory. It is shown that in solutions and in the crystalline state these compounds exist in a ''chair'' conformation with an equatorial orientation of the substituents in the 2 and 4 positions; the high degree of crimped character of the heteroring (the angle of inflection along the 0...0 line is 70.3/sup 0/) is due to repulsion of the unshared electron pairs of the N and O atoms and n-o* interactions. An increase in the n-o* interaction in dialkoxy amines and acetals on passing from C /SUB s/ to C/sub 2/ symmetry of the molecules was demonstrated.
- Research Organization:
- Institute of Chemical Physics, Acad. of Sci., Chernogolovka
- OSTI ID:
- 7005806
- Journal Information:
- Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 21:10; ISSN CHCCA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
AZINES
CATALYTIC EFFECTS
CHEMICAL BONDS
CHEMICAL SHIFT
COHERENT SCATTERING
DIFFRACTION
ELEMENTS
HETEROCYCLIC COMPOUNDS
LCAO METHOD
NITROGEN
NMR SPECTRA
NONMETALS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
SCATTERING
SPECTRA
SPECTROSCOPY
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS
X-RAY DIFFRACTION