Molecular Recognition by Pillar[5]arenes: Evidence for Simultaneous Electrostatic and Hydrophobic Interactions
Borja Gómez-González,
Luis García-Río,
Nuno Basílio,
Juan C. Mejuto,
Jesus Simal-Gandara
Affiliations
Borja Gómez-González
Departamento de Química Física, Facultade de Química, Universidade de Santiago de Compostela, 15782 Santiago, Spain
Luis García-Río
Departamento de Química Física, Facultade de Química, Universidade de Santiago de Compostela, 15782 Santiago, Spain
Nuno Basílio
Laboratório Associado Para a Química Verde (LAQV), Rede de Química e Tecnologia (REQUIMTE), Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal
Juan C. Mejuto
Department of Physical Chemistry, Faculty of Science, University of Vigo, 32004 Ourense, Spain
Jesus Simal-Gandara
Nutrition and Bromatology Group, Analytical and Food Chemistry Department, Faculty of Food Science and Technology, University of Vigo, 32004 Ourense, Spain
The formation of inclusion complexes between alkylsulfonate guests and a cationic pillar[5]arene receptor in water was investigated by NMR and ITC techniques. The results show the formation of host-guest complexes stabilized by electrostatic interactions and hydrophobic effects with binding constants of up to 107 M−1 for the guest with higher hydrophobic character. Structurally, the alkyl chain of the guest is included in the hydrophobic aromatic cavity of the macrocycle while the sulfonate groups are held in the multicationic portal by ionic interactions.
