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Lanthanide shift reagents. IX . Proton and carbon magnetic resonance study of specific contact interactions of a bifunctional oxazole amide with fluorinated lanthanide shift reagents
Author(s) -
Rackham David M.,
Cockerill Anthony F.,
Harrison Roger G.
Publication year - 1978
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270110812
Subject(s) - lanthanide , reagent , chemistry , oxazole , bifunctional , amide , proton , inorganic chemistry , photochemistry , organic chemistry , ion , catalysis , physics , quantum mechanics
Highly specific proton line‐broadening and paramagnetic 13 C shifts observed for N‐butyl‐N(4‐methyloxazol‐2‐yl)‐2‐methylpropionamide in the presence of fluorinated lanthanide shift reagents, are absent when non‐fluorinated reagents are used. This unusual behaviour is rationalized in terms of possible chelation of the N ‐butyl‐ N (4‐methyloxazol‐2‐yl)‐2‐methylpropionamide to the lanthanide reagent, causing transfer of the unpaired electron into the heterocyclic ring.