A new series of heteroaromatic receptors containing the 1,3-bis(6-oxopyridazin-1-yl)propane unit: their selective transport ability towards NH4+ in relation to Na+, K+ and Ca2+

Autor:	Ana Cotillas, Oscar Jaúregui, Fernando Gómez-Contreras, María J. R. Yunta, Carmen Cano, Mercedes Pardo, Pilar Navarro, Lucrecia Campayo, Ana M. Sanz
Rok vydání:	2004
Předmět:	Hydrogen bond Stereochemistry Organic Chemistry Biochemistry Medicinal chemistry Ion Metal chemistry.chemical_compound chemistry Propane Intramolecular force visual_art Drug Discovery Pyridine visual_art.visual_art_medium Ammonium Selectivity
Zdroj:	Tetrahedron. 60:979-986
ISSN:	0040-4020
DOI:	10.1016/j.tet.2003.11.040
Popis:	The synthesis of a new series of heteroaromatic macrocycles 6 – 9 containing the 1,3-bis(6-oxopyridazin-1-yl)propane and pyridine units is reported. The acyclic compounds 11 – 15 had to be prepared as the intermediates in the synthetic sequence. Evaluation of the ionophoric properties of 6 – 9 and 11 – 15 shows that 8 and 13 behave as good ammonium ion carriers and exhibit a high selectivity for ammonium with respect to spherically symmetric metallic ions like Na + , K + , and Ca 2+ . Molecular modelling of the ammonium complexes suggests that the host's oxyimino groups play a more relevant part in effective complexation than the pyridine unit, and that the high complexating efficiency of 13 might be related to the formation of a pseudocavity by intramolecular hydrogen bonding.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c4aa88498f3e579f9e6282c8aa143777 https://doi.org/10.1016/j.tet.2003.11.040 Zobrazit plný text záznamu Full Text from ScienceDirect