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Azonia spiro polyaza macrocycles containing biphenyl subunits as anion and cation receptors
dc.contributor.author | Burguete, M. Isabel | |
dc.contributor.author | Clares, M. Paz | |
dc.contributor.author | García España, Enrique | |
dc.contributor.author | Luis, Santiago V. | |
dc.contributor.author | Querol, Manel | |
dc.contributor.author | Martí-Centelles, Vicente | |
dc.date.accessioned | 2012-09-06T06:37:33Z | |
dc.date.available | 2012-09-06T06:37:33Z | |
dc.date.issued | 2011-06-24 | |
dc.identifier.citation | Tetrahedron (2011), vol. 67, no. 25, p. 4655–4663 | |
dc.identifier.issn | 0040-4020 | |
dc.identifier.uri | http://hdl.handle.net/10234/46043 | |
dc.description.abstract | The reaction of N-Boc triprotected cyclam with bis(chloromethyl)biphenyl followed by the corresponding deprotection of the nitrogen atoms allows the preparation of receptor 3 containing an azonia spiro subunit. This receptor shows slightly increased basicity than cyclam, in particular for the formation of the appropriate triply charged species as a consequence of the reduced capacity of the structure present in 3 to stabilize the species with lower protonation degrees through the formation of intramolecular hydrogen bonds. The properties of 3 as a receptor for Cu2+ and Zn2+ and the anions derived from and ATP have been studied by pH-metric titrations carried out in aqueous solution. While Cu2+ forms a CuL2+ complex and two hydroxylated species of moderate stability, Zn2+ forms only hydroxylated complexes. The association constants obtained for the 1:1 A:L anion complexes denote significant stability for Pi, PPi and ATP; the stability of the H5LA complex found in the case of TPP being lower. 1H NMR spectra for the ATP:L carried out at pD=5.8 show features attributable to the occurrence of intermolecular π–π stacking between the biphenyl unit of 3 and the adenine ring of the nucleotide. DFT calculations have been carried out to rationalize some of the results found, in particular the remarkable different basicity between receptor 3 and cyclam. | ca_CA |
dc.format.extent | 9 p. | ca_CA |
dc.format.mimetype | application/pdf | ca_CA |
dc.language | eng | ca_CA |
dc.language.iso | cat | ca_CA |
dc.publisher | Elsevier | ca_CA |
dc.rights | © 2011 Elsevier Inc. All rights reserved | ca_CA |
dc.rights.uri | http://rightsstatements.org/vocab/InC/1.0/ | * |
dc.subject | Supramolecular chemistry | ca_CA |
dc.subject | Macrocycles | ca_CA |
dc.subject | Polyaza cyclophanes | ca_CA |
dc.subject | Anion recognition | ca_CA |
dc.subject | Metal complexes | ca_CA |
dc.title | Azonia spiro polyaza macrocycles containing biphenyl subunits as anion and cation receptors | ca_CA |
dc.type | info:eu-repo/semantics/article | ca_CA |
dc.identifier.doi | http://dx.doi.org/10.1016/j.tet.2011.04.071 | |
dc.rights.accessRights | info:eu-repo/semantics/restrictedAccess | ca_CA |
dc.relation.publisherVersion | http://www.sciencedirect.com/science/article/pii/S004040201100593X | ca_CA |
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