Winged-cone conformation in hexa- p-tert-butylcalix[6]arene driven by the unusually strong guest encapsulation

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dc.creatorFelipe Terra Martins
dc.creatorBreno Germano de Freitas Oliveira
dc.creatorAriel Marcelo Sarotti
dc.creatorÂngelo de Fátima
dc.date.accessioned2024-08-02T22:28:41Z
dc.date.accessioned2025-09-08T22:52:23Z
dc.date.available2024-08-02T22:28:41Z
dc.date.issued2017
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.description.sponsorshipOutra Agência
dc.format.mimetypepdf
dc.identifier.doihttps://doi.org/10.1021/acsomega.7b00900
dc.identifier.issn2470-1343
dc.identifier.urihttps://hdl.handle.net/1843/72498
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofACS Omega
dc.rightsAcesso Aberto
dc.subjectCalixarenos
dc.subjectEstrutura molecular
dc.subjectMoléculas
dc.subjectSulfoxidos
dc.subjectFuncionais de densidade
dc.subject.otherConformation
dc.subject.otherEnergy
dc.subject.otherMolecular structure
dc.subject.otherMolecules
dc.subject.otherSolvates
dc.subject.otherCalixarenes
dc.titleWinged-cone conformation in hexa- p-tert-butylcalix[6]arene driven by the unusually strong guest encapsulation
dc.typeArtigo de periódico
local.citation.epage5323
local.citation.issue8
local.citation.spage5315
local.citation.volume2
local.description.resumoHexa-p-tert-butylcalix[6]arene (1) is believed to adopt a winged conformation in a solution, featured by four phenyl rings perpendicular to the calix basis and two others at 1,4-positions lying down. However, there is some controversy on the occurrence of this conformation because it has never been found in the solid state of calix[6]arenes, regardless of the substitution pattern at lower and upper rims. Here, we have observed the winged-cone conformation for the first time in a solvate form of 1 with dimethyl sulfoxide (DMSO), dimethylformamide, and pyridine. The DMSO molecule is strongly encapsulated into 1 through two OH···O hydrogen bonds with both flattened phenolic moieties, one lp(S)···π and four CH···π interactions with the four perpendicular phenyl rings. This host–guest complex has energy lower by 23.4 kcal mol–1 than the isolated species. In addition, another DMSO solvate form with 1,2,3-alternate conformation was also obtained in this study, and its structure is compared with that of the precedent one. A detailed density functional theory study has also been carried out to understand the energetic relationships among cone conformers, intramolecular hydrogen-bonding patterns, and DMSO encapsulation.
local.identifier.orcidhttps://orcid.org/0000-0001-9004-0927
local.identifier.orcidhttps://orcid.org/0000-0003-2850-9581
local.identifier.orcidhttps://orcid.org/0000-0002-8151-0306
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://pubs.acs.org/doi/10.1021/acsomega.7b00900

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