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Trends in Organic Chemistry   Volumes    Volume 11 
Abstract
Evaluation of the substituent constants for amino groups based on 19F NMR chemical shifts of p-fluoroanilines
Anna Zakrzewska, Ryszard Gawinecki, Erkki Kolehmainen
Pages: 9 - 16
Number of pages: 8
Trends in Organic Chemistry
Volume 11 

Copyright © 2006 Research Trends. All rights reserved

ABSTRACT
 
Chemical shift of the fluorine atom, d(19F), in the series of p-fluoro substituted aromatic amines were used to calculate the  substituent constants for different amino groups. 1-Pyrrolidino group has the highest electron-donor properties among different amino groups studied. 1-Piperidino group is rather weak electron-donor. On the other hand, the amino nitrogen atoms in N,N-diethylaniline,  1-methyl-1,2,3,4-tetrahydroquinoline and julolidine are strong electron-donors. The nitrogen atom in 1-methylindoline is much weaker donor. ortho-Methyl diminish the donor properties of the N,N-dimethylamino group but it does not affect the unsubstituted amino group. The amino nitrogen atom in 1,2,3,4-tetrahydroquinolines is a stronger electron-donor than that in indolines. The calculated substituent constants of the amino groups studied are consistent with the spectral and reactivity data available in literature.  
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