Molecular Torsion Balances: Evidence for Favorable Orthogonal Dipolar Interactions Between Organic Fluorine and Amide Groups | Zendy

Fischer Felix R. | Zendy; Schweizer W. Bernd | Zendy; Diederich François | Zendy

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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.

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