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Please use this identifier to cite or link to this item: http://hdl.handle.net/1843/49485
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dc.creatorWillian Xerxes Coelho Oliveirapt_BR
dc.creatorWallace Doti do Pimpt_BR
dc.creatorCarlos Basílio Pinheiropt_BR
dc.creatorYves Journauxpt_BR
dc.creatorMiguel Julvept_BR
dc.creatorCynthia Lopes Martins Pereirapt_BR
dc.date.accessioned2023-02-02T18:19:31Z-
dc.date.available2023-02-02T18:19:31Z-
dc.date.issued2019-
dc.citation.volume21pt_BR
dc.citation.issue17pt_BR
dc.citation.spage2818pt_BR
dc.citation.epage2833pt_BR
dc.identifier.doihttps://doi.org/10.1039/C9CE00215Dpt_BR
dc.identifier.issn1466-8033pt_BR
dc.identifier.urihttp://hdl.handle.net/1843/49485-
dc.description.resumoThis work describes the synthesis and characterization of a new class of oxamic acid derivatives containing pyrazole and isoxazole as substituents to investigate their ability to form hydrogen bonds aiming at applying them in crystal engineering and molecular self-recognition. In this respect, we report a new synthesis of 2-(4-nitrophenyl)-1,3-propanedial (1) in high yield using SOCl2 as a chlorinating agent. The new oxamic esters 4-(1H-pyrazol-4-yl)phenylene-N-(ethyloxamate) (2d) and 4-(1,2-oxazol-4-yl)phenylene-N-(ethyloxamate) (3d) were prepared from 1. The synthetic route consists of the cyclisation of 1 either with hydrazine to afford 4-(-aminophenyl)-1H-pyrazole (2a) or with hydroxylamine to obtain the isoxazole-based molecule 4-(4-nitrophenyl)-1,2-oxazole (3a). The reduction of 2a and 3a was carried out in an acidic/tin solution to yield 4-(4-ammoniophenyl)-1H-pyrazol-2-ium trichlorostannate(II) chloride monohydrate (2b) and 4-(4-ammoniophenyl)-1,2-oxazole hexachlorostannate(IV) (3b). Basic extraction of 3b provided 4-(4-aminophenyl)-1,2-oxazole (3c). The reduction of 2a to 4-(4-aminophenyl)-1H-pyrazole (2c) was achieved by means of hydrazine associated with supported palladium on carbon. The condensation of 2c and 3c with ethyl chlorooxoacetate delivers oxamic esters 2d and 3d. In n-tetrabutylammonium hydroxide solution 2d is fully hydrolyzed, obtaining the n-tetrabutylammonium salt of 4-(1H-pyrazole-4-yl)phenylene-N-oxamate as a hemihydrate (2e). The low stability of isoxazole molecules in basic solutions was proved by crystallizing the n-tetrabutylammonium salt of 1-cyano-1-(4-nitrophenyl)-2-oxoethanide (3f) (obtained by cleavage of 3d with n-Bu4NOH) and preparing its conjugated acid 2-(4-nitrophenyl-3-oxopropanenitrile (3e). The structures of 2b, 3b, 3d and 2e were solved by single crystal X-ray diffraction techniques. The analysis of their crystal packing reveals hydrogen bond features compatible for all compounds as well as some differences depending on the pH of the crystallization solution and the presence or absence of the oxamate group due to the increase of hydrogen bond donors and acceptors.pt_BR
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológicopt_BR
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Geraispt_BR
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorpt_BR
dc.description.sponsorshipOutra Agênciapt_BR
dc.languageengpt_BR
dc.publisherUniversidade Federal de Minas Geraispt_BR
dc.publisher.countryBrasilpt_BR
dc.publisher.departmentICX - DEPARTAMENTO DE FÍSICApt_BR
dc.publisher.departmentICX - DEPARTAMENTO DE QUÍMICApt_BR
dc.publisher.initialsUFMGpt_BR
dc.relation.ispartofCrystEngCommpt_BR
dc.rightsAcesso Restritopt_BR
dc.subjectCrystal engineeringpt_BR
dc.subjectOxamic acidpt_BR
dc.subjectHydrogen bondpt_BR
dc.subjectAnilinept_BR
dc.subjectPhenyloxamatept_BR
dc.subjectPyrazolept_BR
dc.subjectIsoxazolept_BR
dc.subject.otherCristalografiapt_BR
dc.subject.otherReconhecimento molecularpt_BR
dc.subject.otherLigação de hidrogêniopt_BR
dc.subject.otherAnilinapt_BR
dc.titleMonitoring the hydrogen bond net configuration and the dimensionality of aniline and phenyloxamate by adding 1H-pyrazole and isoxazole as substituents for molecular self-recognitionpt_BR
dc.typeArtigo de Periódicopt_BR
dc.url.externahttps://pubs.rsc.org/en/content/articlelanding/2019/CE/C9CE00215Dpt_BR
dc.identifier.orcidhttps://orcid.org/0000-0003-0722-5352pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-0281-9592pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-8674-1779pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0003-1587-5718pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0001-9006-8268pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-3799-8092pt_BR
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