ISSN:
0749-1581
Keywords:
Through-space coupling
;
Tetrahydroindazoles
;
Protoporphyrinogen oxidase
;
Molecular mechanics
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
1H, 13C and 19F NMR experiments for a series of 3-alkyl-2-phenyl-4,5,6,7-tetrahydroindazoles revealed a six-bond through-space coupling between the ortho-fluorine and the hydrogen or fluorine atom of the position 3-alkyl group. This was further supported by NOE experiments. Molecular mechanics calculations on a representative structure indicated that several low energy conformers met the fluorine-carbon distance constraint suggested by the NMR data, and dynamic annealing experiments produced a conformer which was in complete agreement with the NMR data. This through-space interaction is speculated to be a result of repulsion between N-1 of the tetrahydroindazole and the ortho-fluorine lone pair electrons.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260310402
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