Please use this identifier to cite or link to this item: https://hdl.handle.net/10316/99941
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dc.contributor.authorNogueira, Bernardo Albuquerque-
dc.contributor.authorCarvalho, Maria-
dc.contributor.authorPaixão, José António de Carvalho-
dc.contributor.authorEusébio, M. Ermelinda-
dc.contributor.authorLopes, Susana Margarida Martins-
dc.contributor.authorMelo, Teresa Margarida Vasconcelos Dias de Pinho e-
dc.contributor.authorFausto, Rui-
dc.date.accessioned2022-04-26T09:04:27Z-
dc.date.available2022-04-26T09:04:27Z-
dc.date.issued2022-01-10-
dc.identifier.issn1466-8033pt
dc.identifier.urihttps://hdl.handle.net/10316/99941-
dc.description.abstractA novel derivative of the prominent ROY compound, 5-acetyl-2-((2-nitrophenyl)amino)thiophene-3-carbonitrile (AcROY), was synthesized in a two-steps procedure by the nucleophilic aromatic substitution reaction between 1-fluoro-2-nitrobenzene and 2-aminothiophene-3-carbonitrile, followed by Friedel–Crafts acylation at position 5 of the thiophene ring. The conformational space of the compound (isolated molecule) was studied computationally, rendering 4 low-energy intramolecularly hydrogen-bonded conformers. The compound exhibits color polymorphism, with 3 different polymorphs identified. The crystal structures of two of the polymorphs were solved by single-crystal X-ray diffraction crystallography: polymorph 1 (burgundy) is monoclinic (P21/n; a = 5.3354(2) Å, b = 14.2344(4) Å, c = 17.1709(6) Å,  = 96.567(2)º, Z = 4, Z’ = 1), and polymorph 2 (orange) is monoclinic (P21/c; a = 25.451(3) Å, b = 14.4966(14) Å, c = 7.1113(7) Å,  = 95.795(6)º, Z = 8, Z’ = 2. It was not possible to determine the crystal structure of the third polymorph (3, orange-yellowish), but the obtained powder X-ray diffraction, infrared and Raman spectroscopy data clearly demonstrate the existence of this additional polymorphic form. Indexation of its powder diffraction pattern showed that it is a monoclinic variety with lattice parameters a = 11.383(3) Å, b = 13.6609(3) Å, c = 25.247(7) Å, β =101.75(1), thus exhibiting a more complex supramolecular structure compared to polymorphs 1 and 2. All polymorphs were characterized spectroscopically (by infrared and Raman spectroscopies) and by thermal analysis (by differential scanning calorimetry and polarized light thermomicroscopy). Interestingly, among the 4 predicted low energy conformers of the AcROY molecule, only the most stable form was found to be present in the crystals of the two structurally characterized polymorphs of the compound. The dominant intermolecular interactions in polymorphs 1 and 2 were investigated (also using Hirshfeld surface analysis) and were found to be significantly different. The observed polymorphism of AcROY is then an interesting case of packing-determined color polymorphism.pt
dc.language.isoengpt
dc.publisherThe Royal Society of Chemistrypt
dc.relationUIDB/00313/2020pt
dc.relationUIDP/00313/2020pt
dc.relationUIDB/04564/2020pt
dc.relationUIDP/04564/2020pt
dc.relationSFRH/BD/129852/2017pt
dc.rightsopenAccesspt
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt
dc.subject5-acetyl-2-((2-nitrophenyl)amino)thiophene-3-carbonitrilept
dc.subjectROYpt
dc.subjectcolor polymorphismpt
dc.subjectmolecular structurept
dc.subjectthermal analysispt
dc.subjectinfrared, Raman and NMR spectroscopiespt
dc.titlePortrayal of the Color Polymorphism in the 5-Acetyl-derivative of ROYpt
dc.typearticle-
degois.publication.firstPage1459pt
degois.publication.lastPage1474pt
degois.publication.issue24pt
degois.publication.titleCrystEngCommpt
dc.peerreviewedyespt
dc.identifier.doi10.1039/d1ce01601fpt
degois.publication.volume24pt
dc.date.embargo2022-01-10*
uc.date.periodoEmbargo0pt
item.cerifentitytypePublications-
item.languageiso639-1en-
item.fulltextCom Texto completo-
item.grantfulltextopen-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.openairetypearticle-
crisitem.author.researchunitFaculty of Sciences and Technology-
crisitem.author.researchunitCFisUC – Center for Physics of the University of Coimbra-
crisitem.author.researchunitCQC - Coimbra Chemistry Centre-
crisitem.author.researchunitCQC - Coimbra Chemistry Centre-
crisitem.author.researchunitCQC - Coimbra Chemistry Centre-
crisitem.author.researchunitCQC - Coimbra Chemistry Centre-
crisitem.author.parentresearchunitUniversity of Coimbra-
crisitem.author.parentresearchunitFaculty of Sciences and Technology-
crisitem.author.parentresearchunitFaculty of Sciences and Technology-
crisitem.author.parentresearchunitFaculty of Sciences and Technology-
crisitem.author.parentresearchunitFaculty of Sciences and Technology-
crisitem.author.orcid0000-0002-1756-377X-
crisitem.author.orcid0000-0003-4634-7395-
crisitem.author.orcid0000-0002-5515-7721-
crisitem.author.orcid0000-0002-1580-5667-
crisitem.author.orcid0000-0003-3256-4954-
crisitem.author.orcid0000-0002-8264-6854-
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