13C NMR Study of 2-Iodoso- and 2-Iodoxy-benzoic Acids and Their Sodium Salts

Article abstract of DOI:10.1002/mrc.1260271102

The 13C NMR spectra for selected 2-iodosobenzoic acids, their sodium salts and the sodium salts of the corresponding iodoxybenzoic acids were measured and carbon assignments made using 2D and NOE experiments and relaxation times.Iodoso and iodoxy groups deshielded the ipso-carbon in these compounds by approximately 25 and 55 ppm, repectively, relative to the corresponding iodo compounds.The 13C NMR spectrs of the 2-iodosobenzoate anions were almost identical with those of the corresponding free acids, both possessing cyclic structures.The iodoxybenzoic acids are either insoluble in, or oxidize, suitable NMR solvents (i.e.DMSO-d6, DMF-d7).The cyclic structure postulated for iodoxybenzoate anions is supported by their 13C chemical shifts.----Key words 13C NMR 2-Iodosobenzoic acids 2-Iodoxybenzoic acids Sodium 2-iodosobenzoates Sodium 2-iodoxybenzoates