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dc.contributor.authorLeigh, David A.
dc.contributor.authorRobertson, Craig C.
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorThomson, Patrick I. T.
dc.date.accessioned2014-08-14T14:01:03Z
dc.date.available2014-08-14T14:01:03Z
dc.date.issued2013-07-03
dc.identifier.citationLeigh , D A , Robertson , C C , Slawin , A M Z & Thomson , P I T 2013 , ' AAAA-DDDD Quadruple Hydrogen-Bond Arrays Featuring NH center dot center dot center dot N and CH center dot center dot center dot N Hydrogen Bonds ' , Journal of the American Chemical Society , vol. 135 , no. 26 , pp. 9939-9943 . https://doi.org/10.1021/ja404504men
dc.identifier.issn0002-7863
dc.identifier.otherPURE: 136329322
dc.identifier.otherPURE UUID: 90ab0f8f-2a1b-4945-9ae1-7ef101e4e4bf
dc.identifier.otherWOS: 000321541800057
dc.identifier.otherScopus: 84879771231
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861731
dc.identifier.urihttp://hdl.handle.net/10023/5159
dc.descriptionThis work is supported by funding from the EPSRC UK.en
dc.description.abstractThe X-ray crystal structure of a previously reported extremely strong quadruple NH center dot center dot center dot N AAAA-DDDD hydrogen-bond array [5.4] (K-a 1.5 x 10(6) M-1 in CH3CN; K-a > 3 x 10(12) M-1 in CH2Cl2) features four short linear hydrogen bonds. Changing the two benzimidazole groups of the DDDD unit to triazole groups replaces two of the NH center dot center dot center dot N hydrogen bonds with CH center dot center dot center dot N interactions (complex [5.6]), but only reduces the association constant in CH3CN by 2 orders of magnitude (K-a = 2.6 x 10(4) M-1 in CH3CN; K-a > 1 x 10(7) M-1 in CH2Cl2). Related complexes without the triazole groups range in K-a from 18 to 270 M-1 in CH3CN, suggesting that the CH center dot center dot center dot N interactions can be considered part of a strong AAAA-DDDD quadruple hydrogen-bonding array. The NH center dot center dot center dot N/CH center dot center dot center dot N AAAA-DDDD motif can be repeatedly switched "on" and "off" in CDCl3 through successive additions of acid and base.
dc.format.extent5
dc.language.isoeng
dc.relation.ispartofJournal of the American Chemical Societyen
dc.rights© 2013. American Chemical Society. This is an article distributed in accordance with the terms of the Creative Commons Attribution (CC BY 4.0) International license, which permits others to distribute, remix, adapt and build upon this work, for noncommercial use, provided the original work is properly citeden
dc.subjectSupramolecular polymersen
dc.subjectTerminal alkynesen
dc.subjectAssociationen
dc.subjectComplexesen
dc.subjectChemistryen
dc.subjectCytosineen
dc.subjectModulesen
dc.subjectAzidesen
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titleAAAA-DDDD Quadruple Hydrogen-Bond Arrays Featuring NH center dot center dot center dot N and CH center dot center dot center dot N Hydrogen Bondsen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1021/ja404504m
dc.description.statusPeer revieweden


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