Correlation of IR parameters with reactivity characteristics for the hydrazides of carboxylic acids |
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Authors: | E. V. Titov A. P. Grekov V. I. Rybachenko V. V. Shevchenko |
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Affiliation: | (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 |
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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 ( 0) Taft constants. Measurements have also been made of the basicity constants at 25 in water and the rate constants for reaction with phenyl isocyanate at 25 . Correlation equations are derived for the transfer of electronic effects across the -CONH-bridge. It is found that the sign of the reaction constant in the correlation of with 0 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. |
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