STUDIES OF STERIC EFFECTS - SPECTROSCOPIC EVIDENCE FOR THROUGH-SPACE INTERACTION IN CH3----O IN CROWDED ALCOHOLS

Authors
TEZUKA T NAKAGAWA M YOKOI K NAGAWA Y YAMAGAKI T NAKANISHI H
Citation
T. Tezuka et al., STUDIES OF STERIC EFFECTS - SPECTROSCOPIC EVIDENCE FOR THROUGH-SPACE INTERACTION IN CH3----O IN CROWDED ALCOHOLS, Tetrahedron letters, 38(24), 1997, pp. 4223-4226
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
24
Year of publication
1997
Pages
4223 - 4226
Database
ISI
SICI code
0040-4039(1997)38:24<4223:SOSE-S>2.0.ZU;2-Y
Abstract
Through-space interaction of the gamma-methyl hydrogen with the oxygen atom in crowded tertiary aliphatic alcohols generates an abnormally l ow-field chemical shift in the O-17 NMR spectra. The intramolecular th rough-space attractive interaction or hydrogen bonding interaction bet ween the gamma-methyl hydrogen and the oxygen lone pair (CH3 ---- O) i s proposed as the cause of this shift. By this interaction, the less p olar C-O bond is generated. (C) 1997 Elsevier Science Ltd.