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Using Dipoles to Control the Directionality of Functional Groups: Syn ‐ and Anti ‐Oriented Benzene‐1,3‐dicarboxamides
Author(s) -
Betson Mark S.,
Clayden Jonathan,
Lam Ho Kam,
Helliwell Madeleine
Publication year - 2005
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.200461787
Subject(s) - dipole , substituent , orientation (vector space) , directionality , benzene , chemistry , yield (engineering) , polar , stereochemistry , crystallography , physics , mathematics , geometry , quantum mechanics , organic chemistry , biology , thermodynamics , genetics
Poles apart : The relative orientation of a pair of functional groups—amides in this case—can be controlled by the choice of the substituent that lies between them. Groups which are effectively cylindrically symmetrical (Me, Cl) allow direct interaction between the dipoles of the amides and induce an anti orientation, whereas polar groups (OCOR, OSO 2 R, SO 2 R) interact with the dipole of both amides to yield a syn orientation (see picture).