Azonia spiro polyaza macrocycles containing biphenyl subunits as anion and cation receptors
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Otros documentos de la autoría: Burguete, M. Isabel; Clares, M. Paz; García España, Enrique; Luis, Santiago V.; Querol, Manel; Martí-Centelles, Vicente
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Mostrar el registro completo del ítemcomunitat-uji-handle:10234/9
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http://dx.doi.org/10.1016/j.tet.2011.04.071 |
Metadatos
Título
Azonia spiro polyaza macrocycles containing biphenyl subunits as anion and cation receptorsAutoría
Fecha de publicación
2011-06-24Editor
ElsevierISSN
0040-4020Cita bibliográfica
Tetrahedron (2011), vol. 67, no. 25, p. 4655–4663Tipo de documento
info:eu-repo/semantics/articleVersión de la editorial
http://www.sciencedirect.com/science/article/pii/S004040201100593XPalabras clave / Materias
Resumen
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 ... [+]
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. [-]
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