Journal
TETRAHEDRON
Volume 65, Issue 35, Pages 7259-7267Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.01.021
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Funding
- JSPS [18350065, 17550012, 19750035, 20550018]
- Ministry of Education, Culture, Sports, Science, and Technology of Japan [19022024]
- Grants-in-Aid for Scientific Research [19022024, 19750035, 20550018, 17550012, 18350065] Funding Source: KAKEN
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The synthesis of calix[4]arene-based molecular containers I and 2 along with the thermodynamic behaviors of cation binding are reported. The containers encapsulated N-methylpicolinium salts to form 1:1 host-guest complexes in chloroform. The thermodynamic investigations of the containers provide contrastive pictures for the process of their guest encapsulations. The encapsulation of I with the N-methylpicolinium cations, bearing a series of counter anions, was primarily enthalpy-driven. The enthalpic difference among the host-guest complexes of the salts was directly related to the total electrostatic stability of the ion-pairs. When 2 encapsulated a series of the N-methylpicolinium cations within its cavity, negative heat capacity changes were observed. This suggests that the changes in the solvation spheres of the container and its guest before and after the formation of the host-guest complex depend on temperature. (C) 2009 Elsevier Ltd. All rights reserved.
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