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RESEARCH ARTICLE

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Configurational Assignment and Conformational Study of Methylglyoxal Bisdimethylhydrazones Derived from the 2-Ethoxypropenal Precursor

Leonid B. Krivdin ^A ^B , Lyudmila I. Larina ^A , Kirill A. Chernyshev ^A and Natalia A. Keiko ^A

+ Author Affiliations

- Author Affiliations

^A A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia.

^B Corresponding author. Email: krivdin@irioch.irk.ru

Australian Journal of Chemistry 59(3) 211-217 https://doi.org/10.1071/CH05309
Submitted: 16 November 2005 Accepted: 21 February 2006 Published: 24 March 2006

Abstract

A configurational assignment of the isomeric methylglyoxal bisdimethylhydrazones derived from the 2-ethoxypropenal precursor has been performed based on experimental measurements and high-level ab initio calculations of ¹J(C,C) and ¹J(C,H) couplings. The results reveal the marked stereochemical dependence upon the orientation of the lone pairs of both nitrogen atoms in different isomers. Methylglyoxal bisdimethylhydrazone is shown to exist in a mixture of the EE and ZE isomers (ca. 75:25), both of which adopt predominant s-trans conformations with minor (up to 8°) out-of-plane deviations.

Acknowledgments

Financial support of the Russian Foundation for Basic Research (grant no. 05-03-32231) is gratefully acknowledged.

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