Polyamide-polyamine cryptand as dicarboxylate receptor : dianion binding studies in the solid state, in solution, and in the gas phase
Chakraborty, Sourav (Indian Association for the Cultivation of Science)
Saha, Subrata (Indian Association for the Cultivation of Science)
Lima, Luis M. P. (Universidade Nova de Lisboa)
Warzok, Ulrike (Freie Universität Berlin)
Sarkar, Sayan (Indian Association for the Cultivation of Science)
Akhuli, Bidyut (Indian Association for the Cultivation of Science)
Nandi, Mandira (Indian Association for the Cultivation of Science)
Bej, Somnath (Indian Association for the Cultivation of Science)
Adarsh, Nayarassery N. (Institut Català de Nanociència i Nanotecnologia)
Schalley, Christoph A. (Freie Universität Berlin)
Delgado, Rita (Universidade Nova de Lisboa)
Ghosh, Pradyut (Indian Association for the Cultivation of Science)

Fecha:	2017
Resumen:	Polyamide-polyamine hybrid macrobicycle L is explored with respect to its ability to bind α,?-dicarboxylate anions. Potentiometric studies of protonated L with the series of dianions from succinate (suc) through glutarate (glu), α-ketoglutarate (kglu), adipate (adi), pimelate (pim), suberate (sub), to azelate (aze) have shown adipate preference with association constant value of K = 4900 M-1 in a HO/DMSO (50:50 v/v) binary solvent mixture. The binding constant increases from glu2- to adi2- and then continuously decreases with the length of the anion chain. Further, potentiometric studies suggest that hydrogen bonding between the guest anions and the amide/ammonium protons of the receptor also contributes to the stability of the associations along with electrostatic interactions. Negative-mode electrospray ionization of aqueous solutions of host-guest complexes shows clear evidence for the selective formation of 1:1 complexes. Single-crystal X-ray structures of complexes of the receptor with glutaric acid, α-ketoglutaric acid, adipic acid, pimelic acid, suberic acid, and azelaic acid assist to understand the observed binding preferences. The solid-state structures reveal a size/shape complementarity between the host and the dicarboxylate anions, which is nicely reflected in the solution state binding studies.
Derechos:	Tots els drets reservats.
Lengua:	Anglès
Documento:	Article ; recerca ; Versió acceptada per publicar
Materia:	Association constant ; Binary solvent mixtures ; Binding constant ; Host guest complexes ; Potentiometric study ; Selective formation ; Single crystal x-ray structures ; Solid-state structures
Publicado en:	Journal of organic chemistry, Vol. 82, Issue 19 (October 2017) , p. 10007-10014, ISSN 1520-6904

DOI: 10.1021/acs.joc.7b01431

Postprint 26 p, 483.8 KB

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