Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/75481
Type: Artigo de periódico
Title: Structural investigations of 5-hydroxy-4,5-dihydroisoxazoles
Author: Campos, PT
Machado, P
Frizzo, CP
Moreira, DN
Meyer, AR
Bonacorso, HG
Zanatta, N
Ducati, LC
Rittner, R
Tormena, CF
Martins, MAP
Abstract: The X-ray diffraction data determined for eight 3-(R-3), 4-(R-4), 4,4-(R-4/R-4') and/or 5-(R-5) 5-hydroxy-4,5-dihydroisoxazoles [where R-3 = Ph, R-4/R-4' = H/H, R-5 = CCl3 (1); R-3 = 4-Br-C6H4, R-4/R-4' = H/H, R-5 = CCl3 (2); R-3 = thien-2-yl, R-4/R-4' = H/H, R-5 = CCl3 (3); R-3 = Ph, R-4 = Ph, R-4' = OH, R-5 = Me (4); R-3 = Me, R-4/R-4' = N-OH, R-5 = Me (5); R-3 = CF3, R-4/R-4' = H/H, R-5 = CMe2CH2OH (6); R-3 = H, R-4 = 4-I-C6H4, R-4' = H, R-5 = 4-I-C6H4 (7): R-3/R-4 = -(CH2)(3)-, R-4' = H, R-5 = CF2CF2H (8);] are discussed. The crystalline structure of compounds 1-3 is described for the first time and crystalline structure of compounds 4-8 has already been described in literature. It was found that the supramolecular auto-organization of 1-8 is characterized by hydrogen bonds invariably involving the hemiacetal hydroxyl group. Compound 5 is the only exception, where the hydroxyl oxime group is the participant in the hydrogen bond. Compounds 4 and 8 present intermolecular contact between the hydroxyl group of the hemiacetal and the nitrogen atom of the 4,5-dihydroisoxazole ring. Compound 7 presents similar interaction, where the hydroxyl contact is with the oxygen atom of the 4,5-dihydroisoxazole ring. Moreover, the crystal structure of compound 6 was stabilized by O-H center dot center dot center dot O interaction between the hydroxyl group of hemiacetal and the hydroxyl group of the alcohol function attached at the 5-position of 4,5-dihydroisoxazole. The crystal structure of compounds 1-3, as described here for the first time, was similar to that of compounds 4 and 7, showing a hydrogen bond O(51)-H(51)center dot center dot center dot N(2) between the hydroxyl group and the nitrogen atom of the isoxazoline ring. This means that the crystal structure of these compounds was governed by hydrogen bonds O-H center dot center dot center dot N, involving the hydroxyl of the hemiacetal group and the nitrogen atom of the 4,5-dihydroisoxazole ring. This interaction is relatively robust, showing a pattern in the crystal packing. Compounds 1-3 also have their crystal stabilized by more weak interactions of type Cl center dot center dot center dot Cl, involving the chlorine atom of the trichloromethyl group. (C) 2011 Elsevier B.V. All rights reserved.
Subject: 4,5-Dihydroisoxazoles
X-ray structure
Hydrogen bonds
Theoretical calculation
Country: Holanda
Editor: Elsevier Science Bv
Rights: fechado
Identifier DOI: 10.1016/j.molstruc.2011.09.051
Date Issue: 2011
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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