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13 C NMR study of 2‐iodoso‐ and 2‐iodoxy‐benzoic acids and their sodium salts
Author(s) -
Katritzky Alan R.,
Duell Bradley L.,
Gallos John K.,
Durst H. Dupont
Publication year - 1989
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.1260271102
Subject(s) - chemistry , sodium salt , carbon 13 nmr , sodium , nmr spectra database , carbon fibers , chemical shift , benzoic acid , nuclear magnetic resonance spectroscopy , proton nmr , organic chemistry , medicinal chemistry , stereochemistry , spectral line , inorganic chemistry , physics , materials science , astronomy , composite number , composite material
The 13 C 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, respectively, relative to the corresponding iodo compounds. The 13 C NMR spectra 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‐ d 6 , DMF‐ d 7 ). The cyclic structure postulated for iodoxybenzoate anions is supported by their 13 C chemical shifts.