Deprotonation of Amides and Polyfunctional Imides Probed by Heteronuclear NMR and Quantum Chemical Calculations

✍ Scribed by Alessandro Bagno; Clara Comuzzi

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 167 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199901)1999:1<287::aid-ejoc287>3.0.co;2-n

✦ Synopsis

The site of deprotonation of several types of amide acids properties (nuclear shielding and electric field gradient) of the involved heteronuclei were calculated and compared (carboxylic amides and imides, sulfonamides, cyanamide, Nhydroxyurea) has been investigated by quantum chemical with experimental 14 N, 17 O and 33 S chemical shifts and relaxation rates. It is shown that the combination of calculations and heteronuclear NMR measurements. Relative energies of tautomeric ions deriving from protonation at the theoretical and experimental tools allows a reliable prediction of spectral parameters and ultimately of the various sites were determined both in the gas phase and in water (by the IPCM continuum solvation method). NMR deprotonation site of polyfunctional acids.

will in turn affect the comparison with experimental data [a] Centro CNR Meccanismi Reazioni Organiche,