N′-(3-Amino-1H-isoindol-1-ylidene)-R-carbohydrazides and Their Amide-Type Isomerism

A series of N′‐(3‐amino‐1H‐isoindol‐1‐ylidene)alkyl(aryl,heteroaryl)carbohydrazides have been synthesized in good yields and their structure and conformational behavior in the solid state and in solution have been studied by X‐ray crystallography, NMR spectroscopy, and quantum calculations. (E)/(Z)...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2006-06, Vol.2006 (12), p.2833-2842
Main Authors: Hordiyenko, Olha V., Biitseva, Angelina V., Kornilov, Mikhail Yu, Brosse, Nicolas, Hocquet, Alexandre, Jamart-Grégoire, Brigitte, Shishkin, Oleg V., Zubatyuk, Roman I.
Format: Article
Language:English
Subjects:
Chemical and Process Engineering
Chemical Sciences
Engineering Sciences
Hydrazones
Materials
Nitrogen heterocycles
NMR spectroscopy
Organic chemistry
Polymers
Quantum calculations
Structure elucidation
X-ray diffraction
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Summary:A series of N′‐(3‐amino‐1H‐isoindol‐1‐ylidene)alkyl(aryl,heteroaryl)carbohydrazides have been synthesized in good yields and their structure and conformational behavior in the solid state and in solution have been studied by X‐ray crystallography, NMR spectroscopy, and quantum calculations. (E)/(Z) amide‐type isomerism and the dependence of the isomeric ratio upon steric effects and solvent polarity are discussed. The thermodynamic parameters of (E) →← (Z) isomerization were determined by 1H NMR dynamic spectroscopy. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200600063