Inter and intra-phase conformerism in two calix [4]arenes

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dc.creatorFernando Machado dos Santos
dc.creatorPatrícia Cruz Souza
dc.creatorJosé Antônio do Nascimento Neto
dc.creatorAna Karoline Silva Mendanha Valdo
dc.creatorLeandro Ribeiro
dc.creatorGuilherme Pereira Guedes
dc.creatorCleiton Moreira da Silva
dc.creatorÂngelo de Fátima
dc.creatorFelipe Terra Martins
dc.date.accessioned2024-10-21T20:23:42Z
dc.date.accessioned2025-09-09T00:50:37Z
dc.date.available2024-10-21T20:23:42Z
dc.date.issued2019
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.identifier.doihttps://doi.org/10.1016/j.molstruc.2019.07.096
dc.identifier.issn0022-2860
dc.identifier.urihttps://hdl.handle.net/1843/77548
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of Molecular Structure
dc.rightsAcesso Restrito
dc.subjectCalixarenos
dc.subjectRaios-X - Difração
dc.subjectCristais
dc.subjectFuncionais de densidade
dc.subject.otherCalix[n]arenes
dc.subject.otherPinched cone conformations
dc.subject.otherConformerism
dc.subject.otherX-ray diffraction
dc.subject.otherFunctionalized iminecalix [4]arene 2
dc.subject.otherDFT calculations
dc.titleInter and intra-phase conformerism in two calix [4]arenes
dc.typeArtigo de periódico
local.citation.spage126849
local.citation.volume1198
local.description.resumoCalix [4]arenes are macrocyclic compounds which can assume four main conformations (cone, partial cone, 1,2-alternate, and 1,3 alternate) driving their desired host-guest ability. Here we report a new polymorph of 25,26,27,28-tetrakis(methoxycarbonylmethoxy)calix [4]arene, which is present with two similar crystallographically independent molecules. These molecules are cone-shaped, in contrast to the 1,3-alternate conformation found in the previously known crystal form of the same compound. Our DFT calculations have also pointed out that the literature 1,3-alternate conformation is more stable than the cone one in the gas phase. Therefore, the higher energy cone conformation is assisted in the solid state by CeH … p contacts, since these interactions occur only in the polymorph described here. We also reported in this study the simultaneous occurrence of two conformations in the crystal lattice of 5,11,17,23- tetra(p fluoroaminobenzylidene)-25,26,27,28-tetrabutoxycalix [4]arene. Pinched cone conformations are assumed through either p … p or CeH … p intramolecular contacts between phenyl rings of the upper rim substituents. These non-covalent contacts are responsible for pointing two alternate phenyl rings from the annulus and their interacted upper rim substituents inwards the cone cavity. DFT calculations reveal that these conformations have very similar energies, helping us to understand the conformerism phenomenon into the elucidated solid state form. Such conformerism found either in two distinct solid state forms or into a same one shows the high conformational complexity of simple calixarenes, which can be decisive to their desired host-guest properties.
local.identifier.orcidhttps://orcid.org/0000-0001-9034-8796
local.identifier.orcidhttps://orcid.org/0000-0002-0967-2300
local.identifier.orcidhttps://orcid.org/0000-0001-6138-9943
local.identifier.orcidhttps://orcid.org/0000-0001-9913-8971
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.identifier.orcidhttps://orcid.org/0000-0001-9004-0927
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.sciencedirect.com/science/article/pii/S0022286019309408

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