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Quantitative Measurements of Edge‐to‐Face Aromatic Interactions by Using Chemical Double‐Mutant Cycles
Author(s) -
Carver Fiona J.,
Hunter Christopher A.,
Jones Philip S.,
Livingstone David J.,
McCabe James F.,
Seward Eileen M.,
Tiger Pascale,
Spey Sharon E.
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20011119)7:22<4854::aid-chem4854>3.0.co;2-#
Subject(s) - face (sociological concept) , mutant , enhanced data rates for gsm evolution , chemistry , process (computing) , biological system , computer science , artificial intelligence , biology , biochemistry , gene , philosophy , linguistics , operating system
Synthetic H‐bonded zipper complexes have been used to quantify the magnitude of an edge‐to‐face aromatic interaction between a benzoyl group and an aniline ring. Four chemical double‐mutant cycles were constructed by using a matrix of nine closely related complexes in which the aromatic rings were sequentially substituted for alkyl substituents. The stability constants and three‐dimensional structures of the complexes were determined by using 1 H NMR titrations in deuterochloroform at room temperature. The value of the interaction energy is similar in all cases, the average is −1.4±0.5 kJ mol −1 . The scope and limitations of the double‐mutant approach are explored, and the consequences of conformational equilibria are discussed.