id,collection,dc.contributor.author,dc.date.accessioned,dc.date.available,dc.date.issued,dc.description.abstract,dc.format.extent,dc.identifier.uri,dc.language,dc.rights.uri,dc.subject.ddc,dc.subject[en],dc.title,dc.type,dcterms.accessRights.openaire,dcterms.bibliographicCitation.articlenumber,dcterms.bibliographicCitation.doi,dcterms.bibliographicCitation.journaltitle,dcterms.bibliographicCitation.number,dcterms.bibliographicCitation.originalpublishername[],dcterms.bibliographicCitation.url,dcterms.bibliographicCitation.volume,dcterms.isPartOf.eissn,refubium.affiliation,refubium.affiliation.other,refubium.resourceType.isindependentpub "e28f0731-fe4e-4ff1-a37b-ecca2c314fb4","fub188/16","Talotta, Carmen||Concilio, Gerardo||Della Sala, Paolo||Gaeta, Carmine||Schalley, Christoph A.||Neri, Placido","2021-02-11T12:21:40Z","2021-02-11T12:21:40Z","2020","The influence of chirality in calixarene threading has been studied by exploiting the “superweak anion approach”. In particular, the formation of chiral pseudo[2]rotaxanes bearing a classical stereogenic center in their axle and/or wheel components has been considered. Two kind of pseudo[2]rotaxane stereoadducts, the “endo-chiral” and “exo-chiral” ones, having the stereogenic center of a cationic axle inside or outside, respectively, the calix-cavity of a chiral calixarene were preferentially formed with specifically designed chiral axles by a fine exploitation of the so-called “endo-alkyl rule” and a newly defined “endo-α-methyl-benzyl rule” (threading of a hexaalkoxycalix[6]arene with a directional (α-methyl-benzyl)benzylammonium axle occurs with an endo-α-methyl-benzyl preference). The obtained pseudorotaxanes were studied in solution by 1D and 2D NMR, and in the gas-phase by means of the enantiomer-labeled (EL) mass spectrometry method, by combining enantiopure hosts with pseudoracemates of one deuterated and one unlabeled chiral axle enantiomer. In both instances, there was not a clear enantiodiscrimination in the threading process with the studied host/guest systems. Possible rationales are given to explain the scarce reciprocal influence between the guest and host chiral centers.","21 S.","https://refubium.fu-berlin.de/handle/fub188/29595||http://dx.doi.org/10.17169/refubium-29339","eng","https://creativecommons.org/licenses/by/4.0/","500 Naturwissenschaften und Mathematik::570 Biowissenschaften; Biologie::570 Biowissenschaften; Biologie","calixarenes||threading||chirality||barfate salts||pseudorotaxane||chiral axles||chiral wheels","Study on the Influence of Chirality in the Threading of Calix[6]arene Hosts with Dialkylammonium Axles","Wissenschaftlicher Artikel","open access","5323","10.3390/molecules25225323","Molecules","22","MDPI","https://doi.org/10.3390/molecules25225323","25","1420-3049","Biologie, Chemie, Pharmazie","Institut für Chemie und Biochemie:::bdaf1c47-f341-464f-b012-0d24067d34b8:::600","no"