Sensitivity of the H/D isotope shifts of the 13C nuclear shielding to the nitrogen lone pair delocalization in anilines and acetanilides
✍ Scribed by Martha S. Morales-Ríos; Pedro Joseph-Nathan
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- English
- Weight
- 425 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
Two-and three-bond deuterium isotope shifts ('A and 'A) of the I3C nuclear shielding were measured for a series of para-substituted anilines and acetanilides, in which the amide NH or the amine NH, hydrogens were partially exchanged with deuterium. The results show that when strong electrondonating groups are present at the para position in acetanilides, the *A(C-l) isotope shifts are smaller than tbe 'A(C-2,6) isotope shifts. Empirical correlations tbat relate 'A isotope shifts with 'H(NH), ''C(C-ipso), "N(NH, or NH), "O(C-0) NMR chemical shifts and witb 'A isotope shifts are presented. The results are interpreted in each series as depending on the Characteristic nitrogen lone pair delocalization.