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A hydrogen-bonded assembly of cucurbit[6]uril and [MoO2Cl2(H2O)(2)] with catalytic efficacy for the one-pot conversion of olefins to alkoxy products

2019-08Journal article Restricted access
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dc.contributor.authorNogueira, Lucie S.
dc.contributor.authorAntunes, Margarida M.
dc.contributor.authorGomes, Ana C.
dc.contributor.authorCunha-Silva, Luis
dc.contributor.authorPillinger, Martyn
dc.contributor.authorLopes, Andre D.
dc.contributor.authorValente, Anabela A.
dc.contributor.authorGoncalves, Isabel S.
dc.date.accessioned2020-07-24T10:51:48Z
dc.date.available2020-07-24T10:51:48Z
dc.date.issued2019-08
dc.description.abstractThe reaction of the macrocyclic cavitand cucurbit[6]uril (CB[6]) and the diaqua complex [MoO2Cl2(H2O)(2)] in hydrochloric acid solution gave a water insoluble supramolecular compound with the general composition 2[MoO2Cl2(H2O)(2)]center dot CB[6]center dot xH(2)O center dot yHCl center dot z(CH3COCH3) (2). Single crystal X-ray diffraction (XRD) analysis revealed the presence of barrel-shape supramolecular entities, {CB[6]center dot 10(H2O)}, aligned in layers which are shifted relative to adjacent layers to form a brick-like pattern. The CB[6]/water hydrogen-bonded entities further engage in intermolecular interactions with water, HCl and [MoO2Cl2(H2O)(2)] molecules to form a three-dimensional (3D) framework. Compound 2 was characterised by thermogravimetric analysis (TGA), IR and Raman vibrational spectroscopy, and C-13{H-1} CP MAS NMR. The reference complex [MoO2Cl2(H2O)(2)]center dot(diglyme)(2) (1) and compound 2 were studied for the oxidative catalytic conversion of olefins (cis-cyclooctene, cyclohexene and styrene) with aqueous H2O2 as oxidant. Using alcohols as solvents, 2 was employed in a one-pot two-stage strategy for converting olefins to alkoxy products, which involves oxidation (with H2O2) and acid chemistry. Mechanistic studies were carried out using different intermediates as substrates, and the type of solvent and substrate scope were investigated. The results demonstrated the ability of the CB[6]/Mo-VI supramolecular adduct to function as an acid-oxidation multifunctional catalyst, and its recovery and reuse via relatively simple procedures.
dc.description.sponsorshipCICECO - Aveiro Institute of Materials [FCT (FundacAo para a Ciencia e a Tecnologia)] [UID/CTM/50011/2019]
dc.description.sponsorshipREQUIMTE-LAQV [UID/QUI/50006/2019]
dc.description.sponsorshipCentre of Marine Sciences - CCMAR [UID/Multi/04326/2019]
dc.description.sponsorshipCENTRO 2020 Regional Operational Programme [CENTRO-01-0145-FEDER-028031, PTDC/QUI-QOR/28031/2017]
dc.description.sponsorshipnational funds through the FCT/MEC
dc.description.sponsorshipEuropean Union (EU) through the European Regional Development Fund under the Portugal 2020 Partnership AgreementEuropean Union (EU)
dc.description.sponsorshipEUEuropean Union (EU) [PD/BD/109666/2015]
dc.description.sponsorshipFCTPortuguese Foundation for Science and Technology
dc.description.sponsorshipnational funds (OE), through FCT
dc.identifier.doi10.1039/c9dt02127b
dc.identifier.issn1477-9226
dc.identifier.issn1477-9234
dc.identifier.urihttp://hdl.handle.net/10400.1/14271
dc.language.isoeng
dc.peerreviewedyes
dc.publisherRoyal Society of Chemistry
dc.subjectCambridge structural database
dc.subjectOxo-molybdenum complexes
dc.subjectCrystal-structures
dc.subjectEfficient catalysts
dc.subjectOxidation
dc.subjectCoordination
dc.subjectCucurbituril
dc.subjectCyclohexene
dc.subjectStyrene
dc.subjectEpoxidation
dc.titleA hydrogen-bonded assembly of cucurbit[6]uril and [MoO2Cl2(H2O)(2)] with catalytic efficacy for the one-pot conversion of olefins to alkoxy products
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage11519
oaire.citation.issue30
oaire.citation.startPage11508
oaire.citation.titleDalton Transactions
oaire.citation.volume48
person.familyNameD. Lopes
person.givenNameAndré
person.identifier2824636
person.identifier.ciencia-id351E-856A-0300
person.identifier.orcid0000-0002-9702-1216
person.identifier.ridE-2136-2012
person.identifier.scopus-author-id7201958625
rcaap.rightsrestrictedAccess
rcaap.typearticle
relation.isAuthorOfPublicationf2f0fe56-e04d-4229-b37b-2b9f1789fe2d
relation.isAuthorOfPublication.latestForDiscoveryf2f0fe56-e04d-4229-b37b-2b9f1789fe2d

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