ISSN:
1434-193X
Keywords:
Ab initio calculations
;
Amides
;
Imides
;
Acidity
;
NMR spectroscopy
;
Deprotonation site
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-The site of deprotonation of several types of amide acids (carboxylic amides and imides, sulfonamides, cyanamide, N-hydroxyurea) has been investigated by quantum chemical calculations and heteronuclear NMR measurements. Relative energies of tautomeric ions deriving from protonation at the various sites were determined both in the gas phase and in water (by the IPCM continuum solvation method). NMR properties (nuclear shielding and electric field gradient) of the involved heteronuclei were calculated and compared with experimental 14N, 17O and 33S chemical shifts and relaxation rates. It is shown that the combination of theoretical and experimental tools allows a reliable prediction of spectral parameters and ultimately of the deprotonation site of polyfunctional acids.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98401_s.pdf or from the author.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
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