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The diphenyliodonium‐2‐carboxylates: An NMR structure investigation
Author(s) -
Mazza Dario Del,
Reinecke Manfred G.,
Smith William B.
Publication year - 1980
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.1270140624
Subject(s) - carboxylate , chemistry , trigonal bipyramidal molecular geometry , proton , group (periodic table) , nuclear magnetic resonance spectroscopy , stereochemistry , medicinal chemistry , ring (chemistry) , crystallography , crystal structure , organic chemistry , physics , quantum mechanics
Diphenyliodonium‐2‐carboxylate, phenyl 4‐methylphenyliodonium‐2‐carboxylate and phenyl 5‐methyl‐phenyliodonium‐2‐carboxylate have been examined by 1 H and 13 C NMR spectroscopy. Each compound showed one proton considerably upfield from the others. From the two substituted compounds this was deduced to be H‐6 on the ring containing the carboxylate group. Shift reagents and relaxation measurements were used to make the 13 C chemical shift assignments. These data are most consistent with a cyclic, neutral structure for these iodonium carboxylates. The iodine is in the center of a trigonal bipyramid with the unsubstituted phenyl and carboxylate group apical, which places the C‐6 proton in the shielding region of the adjacent phenyl group.