ISSN:
0749-1581
Keywords:
1H NMR
;
19F NMR
;
Configurational assignment
;
β-Fluoro-β-phenylamines
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 1H and 19F NMR parameters [δH-α, δH-β, δF, 3J(HH) and 3J(FH)] of β-fluoro-β-phenylamines of the two series PhCHFCH2NR1R2 and PhCHFCH(R)-NR1R2 in CDCl3 (amine form) and in CD3OD (protonated amine form) and those of the corresponding β-hydroxy-β-phenylamines were measured. It is shown that for the protonated amines the predominant conformation is that in which the ammonium group is antiperiplanar to the phenyl group, especially for tertiary amines. Assignment of the diastereoisomers of the PhCHFCHRNR1R2 series can be made with the NMR parameters of the protonated amines: high (low) 3J(HH) values, low (high) 3J(FH) values, 19F chemical shifts to high (low) frequency are those for the threo (erythro) isomers.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260260718
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