Cover Image

COMPLETE ASSIGNMENT OF 1H- AND 13C-NMR SPECTRA OF ANTHRANILIC ACID AND ITS HYDROXY DERIVATIVES AND SALICYLIC ACID AND ITS AMINO DERIVATIVES

Ana B. Miltojević, Niko S. Radulović

DOI Number
-
First page
121
Last page
132

Abstract


We report on the detailed NMR spectral analyses of amino- or/and hydroxy-substituted benzoic acids: anthranilic (AA), 3-hydroxyanthranilic (3-HAA), 5-hydroxyanthranilic (5-HAA), salicylic (SA), 4-aminosalicylic (4-ASA) and 5-aminosalicylic (5-ASA) acids. According to a literature survey, there are limited, unassigned or even incorrectly assigned spectral data to these benzoic acid derivatives. In order to amend the situation, a complete assignment of 1H- and 13C-NMR spectra of these compounds, recorded in perdeuteriodimethyl sulfoxide (DMSO-d6), based on a combination of 1D- and 2D-NMR experiments, including 1H-1H COSY, NOESY, HSQC and HMBC, was performed.

 

POTPUNA ASIGNACIJA 1H- I 13C-NMR SPEKTARA ANTRANILNE KISELINE I NJENIH HIDROKSI-DERIVATA I SALICILNE KISELINE I NJENIH AMINO-DERIVATA


U ovom radu dati su NMR podaci za antranilnu (AA), salicilnu (SA) i regioizomerne (amino)hidroksibenzoeve kiseline, 3-hidroksiantranilnu (3-HAA), 5-hidroksiantranilnu (5-HAA), 4-aminosalicilnu (4-ASA) i 5-aminosalicilnu (5-ASA) kiselinu. Kako je pretragom literature utvrđeno da su do sada objavljeni NMR podaci za pomenute derivate benzoeve kiseline nepotpuni, neasignirani ili čak i pogrešno asignirani, izvršena je kompletna asignacija signala u 1H- i 13C- NMR spektrima snimljenim u deuterisanom dimetil-sulfoksidu (DMSO-d6) kombinovanjem 1H- i 13C-NMR sa 1H-1H COSY, NOESY, HSQC i HMBC eksperimentima.

 

HIGHLIGHTS

  • The NMR spectra of anthranilic, 3- and 5-hydroxyanthranilic, salicylic, 4- and 5-aminosalicylic acids were recorded in DMSO-d6.
  • A literature survey revealed limited, unassigned or even incorrectly assigned spectral data for these amino- or/and hydroxy-substituted benzoic acids.
  • Complete assignment of NMR spectral data was based on a combination of 1H-and 13C-NMR 1D- and 2D-experiments (1H–1H COSY, NOESY, HSQC, HMBC).
  • The 13C-1H coupling constants, previously unavailable in the literature, were derived from the proton-coupled 13C NMR spectra.
  • In the 1H-coupled 13C NMR spectrum of 5-aminosalicylic acid two signals appeared as second-order multiplets, although first-order ones were expected.

Full Text:

PDF


DOI: https://doi.org/10.2298/fu%20pct.v13i2.1297

Refbacks

  • There are currently no refbacks.


ISSN 0354-4656 (print)

ISSN 2406-0879 (online)