Bringing a Molecular Plus One : Synergistic Binding Creates Guest-Mediated Three-Component Complexes
Taimoory, S. M., Twum, K., Dashti, M. A. P., Lahtinen, M., Rissanen, K., Puttreddy, R., Trant, J. F., & Beyeh, N. K. (2020). Bringing a Molecular Plus One : Synergistic Binding Creates Guest-Mediated Three-Component Complexes. Journal of Organic Chemistry, 85(9), 5884-5894. https://doi.org/10.1021/acs.joc.0c00220
Published inJournal of Organic Chemistry
DisciplineOrgaaninen kemiaEpäorgaaninen ja analyyttinen kemiaOrganic ChemistryInorganic and Analytical Chemistry
© 2020 American Chemical Society
C-Ethyl-2-Methylresorcinarene (A), pyridine (B), and a set of ten carboxylic acids (Cn) associate to form A·B·Cn ternary assemblies with 1:1:1 stoichiometry, representing a useful class of ternary systems where the guest mediates complex formation between the host and a third component. Although individually weak in solution, the combined strength of the multiple non-covalent interactions organizes the complexes even in a highly hydrogen-bond competing methanol solution as explored by both experimental and computational methods. The interactions be-tween A·B and Cn are dependent on the pKa values of carboxylic acids. The weak interactions between A and C further reinforce the interactions between A and B, demonstrating positive cooperativity. Our results reveal that the two-component system such as that formed by A and B can form the basis for the development of specific sensors for the molecular recognition of carboxylic acids.
PublisherAmerican Chemical Society
Publication in research information system
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Related funder(s)Academy of Finland
Funding program(s)Postdoctoral Researcher, AoF
Additional information about fundingThe authors gratefully acknowledge financial support from the Academy of Finland (RP: grant# 298817), the University of Jyväskylä, Natural Sciences and Engineering Research Council of Canada (JFT: grant # 2018-06338), National Natural Science Foundation of China (FP: grant# 21602071) and Oakland University, MI, USA. This work was made possible by the facilities of the Shared Hierarchical Academic Research Compu-ting Network (SHARCNET: www.sharcnet.ca) and Compute/Calcul Canada. ...
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