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Combined Cation–π and Anion–π Interactions for Zwitterion Recognition
Author(s) -
Perraud Olivier,
Robert Vincent,
Gornitzka Heinz,
Martinez Alexandre,
Dutasta JeanPierre
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201106934
Subject(s) - zwitterion , ion , titration , chemistry , molecular recognition , host (biology) , computational chemistry , inorganic chemistry , molecule , organic chemistry , biology , ecology
Brothers and enemies : Anion–π and cation–π interactions act in a synergistic way when gathered in the molecular cavity of a hemicryptophane host, affording an efficient contribution (−170 kJ mol −1 ) in zwitterion recognition. NMR titration experiments and calculations reveal the positioning of the guest in the cavity of the heteroditopic receptor. This study emphasizes the importance of anion–π bonds in host–guest chemistry.