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RESEARCH ARTICLE
Contents Vol 72(9)

Prototropic Tautomerism and Some Features of the IR Spectra of 2-(3-Chromenyl)-1-hydroxyimidazoles

Polina A. Nikitina https://orcid.org/0000-0003-1542-5565 A B D , Tatiana Yu. Koldaeva A , Vitaly S. Mityanov A C , Vladimir S. Miroshnikov A , Elizaveta I. Basanova A and Valery P. Perevalov A
+ Author Affiliations
- Author Affiliations

A Department of Fine Organic Synthesis and Chemistry of Dyes, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya square 9, Moscow, 125047, Russia.

B A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova street 28, Moscow, 119991, Russia.

C N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky avenue 47, Moscow, 119991, Russia.

D Corresponding author. Email: polinandrevna@yandex.ru

Australian Journal of Chemistry 72(9) 699-708 https://doi.org/10.1071/CH19222
Submitted: 15 May 2019  Accepted: 14 June 2019   Published: 9 July 2019

Abstract

Prototropic tautomerism of 2-(3-chromenyl)-1-hydroxyimidazoles with various substituents in the chromenyl moiety (1-hydroxyimidazole – imidazole N-oxide) was studied by means of 1H NMR and IR spectroscopies. It was demonstrated that in d6-DMSO solution, the substituents in the chromenyl ring have no influence on the equilibrium shift: the prevalence of the N-oxide tautomeric form is caused by the possibility of stabilization of the planar structure with the help of the carbonyl group in position 5 of the imidazole ring. In contrast, in the solid state the general effect of the chromenyl substituent in position 2 of imidazole plays the leading role. The increase in general electron-withdrawing effect of the chromenyl moiety leads to the prevalence of the imidazole N-oxide tautomer.


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