Structure and bonding in cyclic phosphoramidates as determined by carbon-13 magnetic resonance
作者:
Gerald W. Buchanan,
Frederick G. Morin,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1979)
卷期:
Volume 57,
issue 1
页码: 21-26
ISSN:0008-4042
年代: 1979
DOI:10.1139/v79-004
出版商: NRC Research Press
数据来源: NRC
摘要:
13C chemical shifts and13C–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.
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