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Understanding the driving force for the molecular recognition of S6-corona[3]arene[3]pyridazine toward organic ammonium cations

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Abstract

The molecular recognition of S6-corona[3]arene[3]pyridazine toward various N-alkyl ammonium cations was systematically studied by means of ITC titration, NMR spectroscopy, mass spectrometry and X-ray crystallography. As a powerful and selective macrocyclic host molecule, S6-corona[3]arene[3]pyridazine was able to form dominantly 1 : 1 complexes with cations in a mixture of CH3CN and 1,2-dichloroethane (v : v = 1 : 1) giving association constants in the range of (1.08 ± 0.01) × 103 M−1 to (1.48 ± 0.11) × 105 M−1. In all cases, the favorable host–guest complexation processes were driven by the combination of beneficial enthalpy and entropy effects. While the enthalpy effect was attributable to the multiple non-covalent bond attractions such as lpe/π, π/π and nonconventional hydrogen bonds between host and guest, the entropy increase was most likely due to the desolvation of the guests.

Graphical abstract: Understanding the driving force for the molecular recognition of S6-corona[3]arene[3]pyridazine toward organic ammonium cations

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Publication details

The article was received on 03 Oct 2017, accepted on 14 Nov 2017 and first published on 15 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QO00900C
Citation: Org. Chem. Front., 2018, Advance Article
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    Understanding the driving force for the molecular recognition of S6-corona[3]arene[3]pyridazine toward organic ammonium cations

    M. Zhao, Q. Guo and M. Wang, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00900C

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