Orientation of the unshared electron pair of the nitrogen atom in N-substituted 2,5-dimethyl-4-piperidinones

1989 ◽  
Vol 25 (4) ◽  
pp. 426-427
Author(s):  
A. �. Aliev ◽  
A. A. Fomichev

1979 ◽  
Vol 57 (1) ◽  
pp. 21-26 ◽  
Author(s):  
Gerald W. Buchanan ◽  
Frederick G. Morin

13C chemical shifts and 13C–31P couplings are reported for 11 cyclic phosphoramidates of ring sizes from four to nine. Vicinal couplings are compared with those of carbocyclic analogs and provide insight regarding the degree of nitrogen lone pair derealization into the N—P bond. For six-membered and larger rings, there appears to be nearly complete lone pair delocalization, i.e., a trigonal planar nitrogen atom. In azetidine derivatives the nitrogen lone pair remains localized, giving rise to a highly puckered ring conformation. Pyrrolidine derivatives are viewed as having a nitrogen with a partially delocalized electron pair.



Author(s):  
L. K. Yuldasheva ◽  
R. P. Arshinova ◽  
S. G. Vul'fson






ChemInform ◽  
2010 ◽  
Vol 24 (29) ◽  
pp. no-no
Author(s):  
B. KAMENAR ◽  
M. BRUVO ◽  
J. BUTUMOVIC


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