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Extensive intramolecular and intermolecular interactions in two quaternary salts of the pyridoxal oxime

Cetina, Mario; Nagl, Ante; Gašo-Sokač, Dajana; Kovač, Spomenka; Bušić, Valentina; Saftić, Dijana (2012) Extensive intramolecular and intermolecular interactions in two quaternary salts of the pyridoxal oxime. Journal of Chemical Crystallography, 42 . pp. 752-758. ISSN 1074-1542

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Abstract

Two derivatives of pyridoxal oxime (1) were prepared by quaternization of pyridoxal oxime with phenacyl bromide and 2-methoxyphenacyl bromide. The crystal structures of the 1-phenacyl-3-hydroxy-4-hydroxyiminomethyl- 5-hydroxymethyl-2-methylpyridinium bromide (2) and the novel 3-hydroxy-4-hydroxyiminomethyl-5-hydroxymethyl-2-methyl-1-(20-methoxyphenacyl) pyridinium bromide (3) have been determined by X-ray diffraction method. The conformation of these two pyridoxal oxime phenacyl derivatives is locked by numerous intramolecular hydrogen bonds. The O–H---Br, C–H---Br and C–H---O hydrogen bonds in 2 and 3 form complex three-dimensional network. Supramolecular structure of 3 also contains C–H---p and p---p interactions which link neighbouring cations.

Item Type: Article
Uncontrolled Keywords: quaternary pyridinium salts; phenacyl bromides; pyridoxal oxime derivatives; X-ray diffraction; supramolecular assembling
Subjects: NATURAL SCIENCES
NATURAL SCIENCES > Chemistry
NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Depositing User: Dijana Saftić
Date Deposited: 02 May 2018 13:16
Last Modified: 02 May 2018 13:16
URI: http://fulir.irb.hr/id/eprint/4023
DOI: 10.1007/s10870-012-0312-y

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