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Structural effects on 17 O NMR shifts of cyclic phosphine oxides
Author(s) -
Quin Louis D.,
Szewczyk Jerzy,
Linehan Kathleen,
Harris David L.
Publication year - 1987
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260250319
Subject(s) - chemistry , phosphine , phosphine oxide , chemical shift , oxygen , oxide , ring (chemistry) , carbon 13 nmr , norbornene , oxygen 17 , nmr spectra database , ring size , proton nmr , crystallography , stereochemistry , organic chemistry , spectral line , nuclear magnetic resonance , monomer , polymer , catalysis , physics , astronomy
The 17 O NMR chemical shifts of a variety of cyclic phosphine oxides were recorded at natural abundance. The shifts proved to be extremely sensitive to structural effects such as ring size and the presence of γ‐interactions. Values were found to cover a 70 ppm range. The most unusual effect was discovered with phosphine oxide groups in the 7‐position of the norbornene framework. When the oxygen was anti to the double bond, exceptionally strong deshielding (by as much as 60 ppm) occurred relative to the isomer with syn oxygen. 17 O NMR clearly has value as a structural diagnostic technique with phosphine oxides.