Mechanochemical and Conformational Study of N-heterocyclic Carbonyl-Oxime Transformations

Primožič, Ines and Hrenar, Tomica and Baumann, Krešimir and Krišto, Lucija and Križić, Ivana and Tomić, Srđanka (2014) Mechanochemical and Conformational Study of N-heterocyclic Carbonyl-Oxime Transformations. Croatica Chemica Acta, 87 (2). pp. 153-160. ISSN 0011-1643

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Abstract

New mechanochemical pathways for the transformation of six N-heterocyclic carbonyl compounds into oximes using hydroxylamine hydrochloride were explored. Reactions were performed first without any base since the heterocyclic moieties (imidazole, benzimidazole, pyridine and quinuclidine) have an intrinsic basic nitrogen atom. This green, solvent free method was suitable for all compounds (up to quantitative yields) except for N-benzyl substituted imidazole and benzimidazole-2-carbaldehyde. For the slower reacting aldehydes, reactions with liquid assisted grinding and addition of sodium hydroxide were performed as well. Conformational analysis and quantum-chemical calculations revealed steric and electronic reasons for the lower reactivity of N-benzyl substituted derivatives.

Item Type: Article
Keywords: nitrogen heterocycles ; oximes; mechanochemical synthesis ; conformational analysis ; DFT
Date: 2014
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Faculty of Science > Department of Chemistry
Publisher: Hrvatsko kemijsko društvo
Related URLs:
Depositing User: mag. bibl. Ana Šafran
Date Deposited: 26 Nov 2014 10:11
Last Modified: 26 Nov 2014 10:11
URI: http://digre.pmf.unizg.hr/id/eprint/3378

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