The diphenyliodonium-2-carboxylates: An NMR structure investigation

Diphenyliodonium-2-carboxylate, phenyl 4-methylphenyliodonium-2-carboxylate and phenyl 5-methyl-phenyliodonium-2-carboxylate have been examined by ¹H and ¹³C 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 ¹³C 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.