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Conference Paper: The idiosyncrasies of tetrabenzo[24]crown-8 in the solid state

TitleThe idiosyncrasies of tetrabenzo[24]crown-8 in the solid state
Authors
KeywordsC-H···π interactions
Crown ethers
Hydrogen bonding
Pseudo-rotaxanes
Supramolecular chemistry
Issue Date2000
Citation
Tetrahedron, 2000, v. 56, n. 36, p. 6675-6681 How to Cite?
AbstractIn the solid state, the macrocyclic polyether tetrabenzo[24]crown-8 (TB24C8) is an interesting molecule. When crystallized from MeCN solution, a bis-MeCN clathrate is formed, in which the TB24C8 macroring - by adopting a conformation with approximate tenms-ball-seam symmetry (D(2d)) - forms C-H···π-linked supramolecular chains. However, when crystallized from CHCl3/Et2O solution, the TB24C8 crystallizes alone - adopting a self-filling 'flattened-out' conformation with C(i) symmetry - forming C-H···π-linked sheets which stack upon one another by virtue of - yet again (!) - C-H···π hydrogen bonds. By contrast, the solid-state superstructure of the [2]pseudorotaxane formed between TB24C8 and dibenzylammonium hexafluorophosphate (DBA.PF6), contains no C-H···π interactions. However, a multitude of more enthalpically favorable C-H···F hydrogen bonds - to a highly-ordered matrix of PF6 anions - stabilizes the formation of the [2]pseudorotaxane array. (C) 2000 Elsevier Science Ltd.
Persistent Identifierhttp://hdl.handle.net/10722/332458
ISSN
2023 Impact Factor: 2.1
2023 SCImago Journal Rankings: 0.406
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorCantrill, Stuart J.-
dc.contributor.authorPreece, Jon A.-
dc.contributor.authorStoddart, J. Fraser-
dc.contributor.authorWang, Zhen He-
dc.contributor.authorWhite, Andrew J.P.-
dc.contributor.authorWilliams, David J.-
dc.date.accessioned2023-10-06T05:11:40Z-
dc.date.available2023-10-06T05:11:40Z-
dc.date.issued2000-
dc.identifier.citationTetrahedron, 2000, v. 56, n. 36, p. 6675-6681-
dc.identifier.issn0040-4020-
dc.identifier.urihttp://hdl.handle.net/10722/332458-
dc.description.abstractIn the solid state, the macrocyclic polyether tetrabenzo[24]crown-8 (TB24C8) is an interesting molecule. When crystallized from MeCN solution, a bis-MeCN clathrate is formed, in which the TB24C8 macroring - by adopting a conformation with approximate tenms-ball-seam symmetry (D(2d)) - forms C-H···π-linked supramolecular chains. However, when crystallized from CHCl3/Et2O solution, the TB24C8 crystallizes alone - adopting a self-filling 'flattened-out' conformation with C(i) symmetry - forming C-H···π-linked sheets which stack upon one another by virtue of - yet again (!) - C-H···π hydrogen bonds. By contrast, the solid-state superstructure of the [2]pseudorotaxane formed between TB24C8 and dibenzylammonium hexafluorophosphate (DBA.PF6), contains no C-H···π interactions. However, a multitude of more enthalpically favorable C-H···F hydrogen bonds - to a highly-ordered matrix of PF6 anions - stabilizes the formation of the [2]pseudorotaxane array. (C) 2000 Elsevier Science Ltd.-
dc.languageeng-
dc.relation.ispartofTetrahedron-
dc.subjectC-H···π interactions-
dc.subjectCrown ethers-
dc.subjectHydrogen bonding-
dc.subjectPseudo-rotaxanes-
dc.subjectSupramolecular chemistry-
dc.titleThe idiosyncrasies of tetrabenzo[24]crown-8 in the solid state-
dc.typeConference_Paper-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/S0040-4020(00)00475-0-
dc.identifier.scopuseid_2-s2.0-0033822766-
dc.identifier.volume56-
dc.identifier.issue36-
dc.identifier.spage6675-
dc.identifier.epage6681-
dc.identifier.isiWOS:000089149100011-

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