Steric structure of alkyl 2-aryl(hetaryl)hydrazono-3-fluoroalkyl-3-oxopropionates / Khudina O. G.,Burgart Ya. V.,Shchegol'kov E. V.,Saloutin V. I.,Kazheva O. N.,Chekhlov A. N.,D'yachenko O. A. // RUSSIAN JOURNAL OF ORGANIC CHEMISTRY. - 2009. - V. 45, l. 6. - P. 801-809.

ISSN/EISSN:

1070-4280 / нет данных

Type:

Article

Abstract:

Steric structure of fluorinated 2-arylhydrazono-3-oxo esters was studied by H-1, F-19, and C-13 NMR spectroscopy and X-ray analysis. It was found that these compounds in the crystalline state and in solutions in acetone-d (6), DMSO-d (6), and CDCl3 exist as Z isomers with the ester fragment involved in intramolecular hydrogen bond with the hydrazone NH proton. Exceptions are alkyl 2-arylhydrazono-4,4-difluoro-3-oxobutanoates which exist in acetone-d (6) as mixtures of Z and E isomers, the former prevailing. Unlike fluorinated analogs, ethyl 2-(4-methylphenyl)hydrazono-3-oxobutanoate in crystal has the structure of E isomer in which intramolecular hydrogen bond is formed between the NH proton and acetyl carbonyl group. The same compound in acetone-d (6), DMSO-d (6), and CDCl3 gives rise to a mixture of Z and E isomers, the latter prevailing.

Author keywords:

CONTAINING 2-ARYLHYDRAZONO-1,3-DICARBONYL COMPOUNDS; O-PHENYLENEDIAMINE; 2-ARYLHYDRAZONES; ETHYLENEDIAMINE

DOI:

10.1134/S1070428009060013

Web of Science ID:

ISI:000267898400001

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUN
Publisher	MAIK NAUKA/INTERPERIODICA/SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013-1578 USA
Language	English
Keywords-Plus	CONTAINING 2-ARYLHYDRAZONO-1,3-DICARBONYL COMPOUNDS; O-PHENYLENEDIAMINE; 2-ARYLHYDRAZONES; ETHYLENEDIAMINE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	saloutin@ios.uran.ru
ResearcherID-Numbers	Shchegol'kov, Evgenii/H-6790-2015 Burgart, Yanina/T-8025-2017
ORCID-Numbers	Shchegol'kov, Evgenii/0000-0001-6611-2855 Burgart, Yanina/0000-0001-6061-2410
Funding-Acknowledgement	Russian Federation {[}3758.2008.3]
Funding-Text	This study was performed under financial support by the Council for Grants at the President of the Russian Federation (program for state support of leading scientific schools, project no. 3758.2008.3).
Number-of-Cited-References	14
Usage-Count-Since-2013	2
Journal-ISO	Russ. J. Organ. Chem.
Doc-Delivery-Number	469KZ