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Correlation of IR parameters with reactivity characteristics for the hydrazides of carboxylic acids
Authors:E V Titov  A P Grekov  V I Rybachenko  V V Shevchenko
Institution:(1) Donetsk Division of Physical Organic Chemistry, Pisarzhevskii Institute of Physical Chemistry, AS UkrSSR, USSR;(2) Institute of the Chemistry of High-Molecular Compounds, AS UkrSSR, USSR;(3) Donetsk State University, USSR
Abstract:Measurements have been made of the frequencies of the N-H and C=O stretching modes in dilute solution in CCl4 for 23 aliphatic and aromatic substituted hydrazides of carboxylic acids. These are compared with the sgr (sgr0) Taft constants. Measurements have also been made of the basicity constants at 25Dagger in water and the rate constants for reaction with phenyl isocyanate at 25Dagger. Correlation equations are derived for the transfer of electronic effects across the -CONH-bridge. It is found that the sign of the reaction constant rgr in the correlation of 
$$\upsilon _{{\text{NH}}_{\text{2}} } $$
with sgr0 reverses on passing from aromatic amines to amides via the hydrazides of carboxylic acids.We are indebted to L. M. Litvinenko and A. F. Popov for a discussion of the results.
Keywords:
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