Conclusions
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1.
The introduction of a phenyl or alkyl substituent at the β-nitrogen atom in the hydrazides of carboxylic acids and their fluorinated analogs leads to a trans orientation of the unshared pairs of electrons on the nitrogen atoms.
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2.
The influence of fluorine atoms on the electronic state of the C=O group in molecules of 1-acyl-2-alkylhydrazines and 1-acyl-2-phenylhydrazines is due to the inductive effect of the substituent R and to the possibility of stabilization by the intramolecular NH...F hydrogen bond.
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3.
The greatest electronic effect of a fluoroalkyl substituent on a hydrazide fragment is realized in the acylhydrazines and 1-acyl-2-phenylhydrazines.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2739–2744, December, 1980.
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Voronkov, M.G., Sarapulova, G.I., Chipanina, N.N. et al. Spectroscopic investigation of the intramolecular effects in the hydrazides of fluoro-substituted carboxylic acids. Russ Chem Bull 29, 1915–1919 (1980). https://doi.org/10.1007/BF00949656
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DOI: https://doi.org/10.1007/BF00949656