ISSN:
0749-1581
Keywords:
9-methoxyfluorene
;
NMR
;
MNDO
;
ab intio calculations
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The results of NMR investigations based on the heteronuclear 3J(CH3, H-9) coupling constant, the methyl group chemical shift, lanthanide-induced shifts and MNDO calculations indicate that 9-methoxyfluorene exists predominantly in the trans conformation in which the methyl group is oriented in an antiperiplanar relationship with respect to H-9. Previous experimental work on the 9-hydroxy analogue demonstrated a similar conformational preference, which is also indicated by the results of MNDO and ab initio calculations presented here. The origin of the preference probably lies in a repulsive interaction between the electrons of the aromatic π-systems and the lone-pair electrons of the hydroxyl or methoxyl oxygen.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260250315
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