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

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]pyridazi...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2018, Vol.5 (5), p.760-764
Main Authors: Meng-Yao, Zhao, Qing-Hui Guo, Mei-Xiang, Wang
Format: Article
Language:English
Subjects:
Ammonium
Cations
Chemical bonds
Crystallography
Dichloroethane
Enthalpy
Entropy
Hydrogen bonding
Hydrogen bonds
Magnetic resonance spectroscopy
Mass spectrometry
Mass spectroscopy
NMR spectroscopy
Organic chemistry
Pyridazines
Recognition
Titration
X-ray crystallography
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/c7qo00900c