English   español  
Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/126251
Compartir / Impacto:
Estadísticas
Add this article to your Mendeley library MendeleyBASE
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Título

The influence of intermolecular halogen bonds on the tautomerism of nucleobases. I. Guanine Dedicated to Professor Paul von Ragué Schleyer, in memoriam

AutorMarín-Luna, Marta; Alkorta, Ibon ; Elguero, José
Fecha de publicación2015
EditorElsevier
CitaciónTetrahedron 71: 5260-5266 (2015)
ResumenIn this paper, we report a computational study of the influence of halogen bonds (XB) on the tautomerism of 9-methylguanine, a model of guanosine and GTP. Molecular Electrostatic Potentials (MEP), interaction energies, Atoms in Molecules (AIM) and Natural Bond Orbitals (NBO) were used to characterize the complexes between three tautomers of 9-methylguanine (one oxo and two hydroxy) and five dihalogens molecules (Br<inf>2</inf>, BrCl, BrF, Cl<inf>2</inf> and ClF). The results concerning the halogen bonds were compared with the effect of hydrogen bonds using hydrogen fluoride as a hydrogen bond donor. The binding energies of the complexes have been analyzed using a Free-Wilson model to obtain the individual interactions. An important conclusion of this study is that halogen bonds are able to strongly modify the order of stability of the three most stable tautomers that, in turn, could induce mutations according to the 'rare tautomer hypothesis'.
Versión del editorhttp://dx.doi.org/10.1016/j.tet.2015.06.023
URIhttp://hdl.handle.net/10261/126251
DOI10.1016/j.tet.2015.06.023
Identificadoresdoi: 10.1016/j.tet.2015.06.023
issn: 1464-5416
Aparece en las colecciones: (IQM) Artículos
Ficheros en este ítem:
Fichero Descripción Tamaño Formato  
accesoRestringido.pdf15,38 kBAdobe PDFVista previa
Visualizar/Abrir
Mostrar el registro completo
 

Artículos relacionados:


NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.