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Molecular Torsion Balances: Evidence for Favorable Orthogonal Dipolar Interactions Between Organic Fluorine and Amide Groups
Author(s) -
Fischer Felix R.,
Schweizer W. Bernd,
Diederich François
Publication year - 2007
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.200702497
Subject(s) - amide , supramolecular chemistry , dipole , chemistry , non covalent interactions , stereochemistry , ligand (biochemistry) , torsion (gastropod) , torsion spring , computational chemistry , crystallography , molecule , hydrogen bond , organic chemistry , receptor , physics , biochemistry , medicine , surgery , classical mechanics
Finding the right balance : An indole‐extended molecular torsion balance has the geometry for measuring a truly orthogonal noncovalent interaction between a CF bond dipole and an amide carbonyl group (see picture, green F, red O, blue N). Employing a double‐mutant cycle approach, negative interaction free enthalpies were determined. Thus orthogonal dipolar interactions can be a new tool for stabilizing protein–ligand complexes and assembling supramolecular architectures.