Please use this identifier to cite or link to this item:
Título : Hydrogen-bond-mediated self-assembly of 26-membered diaza tetraester crowns of 3,5-disubstituted 1 h -pyrazole. Dimerization study in the solid state and in CDCl3 solution
Autor : Reviriego, Felipe, Navarro, Pilar, Arán, Vicente J., Jimeno, M. Luisa, García-España, Enrique, Latorre, Julio, Yunta, María J. R.
Fecha de publicación : 2011
Editor: American Chemical Society
Resumen: By using an improved synthetic method reported earlier, the cyclic stannoxanes obtained from RN-diethanolamine (R = Me, Bu) and dibutyltin oxide have been reacted with 1H-pyrazole-3,5-dicarbonyl dichloride to afford 26-membered diaza tetraester crowns (1, R = Me; 3, R = Bu) and 39-membered triaza hexaester crowns (2, R = Me; 4, R = Bu). The new structures were identified from their analytical and spectroscopic (1H and 13C NMR, FAB-MS, and/or ESI-MS) data. Both diaza tetraester crowns (1 and 3), containing two 1H-pyrazole units, self-assemble into dimeric species through the formation of four hydrogen bonds involving the two NH pyrazole groups and the two tertiary amine groups of both crowns, as proved by X-ray crystallography and NMR analysis. Preliminary NMR, ESI-MS, MALDI-TOF-MS, and molecular modeling studies suggest that, in CDCl3 solution, 1 interacts with ethyleneurea (ETU), affording 1:1, 2:1, and 2:2 1-ETU complexes. © 2011 American Chemical Society.
Identificadores: doi: 10.1021/jo2012835
issn: 0022-3263
Citación : Journal of Organic Chemistry 76: 8223- 8231 (2011)
Appears in Collections:(CENQUIOR) Artículos

Files in This Item:
File Description SizeFormat 
accesoRestringido.pdf15,38 kBAdobe PDFView/Open
Show full item record

Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.