ISSN:
0749-1581
Keywords:
Hydroxybicyclo[2.2.1]heptenes and -heptanes
;
17O NMR chemical shifts
;
Substituent effects
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Well resolved natural abundance 17O NMR spectra of 27 mono-, di-, tri- and tetrahydroxybicyclo[2.2.1]heptenes and -heptanes (norbornenes or norbornanes), their methylated derivatives and some related compounds were measured for 0.5 M or saturated solutions in acetonitrile at 65°C. In addition, the 17O NMR chemical shifts of 14 aliphatic and alicyclic alcohols were also determined for reference purposes. The 17O NMR chemical shifts of all compounds were assigned. Both methyl- and hydroxyl-induced deshielding β-effects were consistent with those reported in the literature. Similarly, observed shielding γ-effects were in agreement with the earlier observations and characteristic especially for mutual γ-gauche and -eclipsed orientations of substituents. In addition, clear shielding δ-effects (up to 10 ppm) were observed in tri- or tetrahydroxynorbornanes. These δ-effects can be related to the attractive van der Waals interactions observed earlier in 13C NMR chemical shifts.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260310814
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