Journal
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
Volume 95, Issue 3, Pages 322-328Publisher
JOHN WILEY & SONS INC
DOI: 10.1002/qua.10760
Keywords
hyperconjugation; hydroxyl group; amine group
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Systematic investigations of conformational effects of the hydroxyl group on carbon or hydrogen chemical shifts of different types of alcohols reveal that, besides stereoelectronic effects, hyperconjugation with lone pairs may have a strong influence. In view of the growing use of chemical shifts in probing the structure of biologic molecules, we employed DFT/GIAO/NBO calculations at the B3LYP level for conformers obtained from partial optimization of structures resulting from 30degrees variations of the C-C-X-H (X==O, N) dihedral angles to verify if nitrogen responded in a fashion similar to oxygen. Although the hybridization and geometry of hydroxyl and amine groups are distinct, the lone pair on nitrogen reveals hyperconjugation with suitably positioned orbitals on alkyl groups. (C) 2003 Wiley Periodicals, Inc.
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