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Cover Picture: Effect of Substituents on the Complexation of Aromatic and Quinoid Substrates with Molecular Tweezers and Clips (Eur. J. Org. Chem. 7/2004)
Author(s) -
Klärner FrankGerrit,
Polkowska Jolanta,
Panitzky Jens,
Seelbach Uta P.,
Burkert Ulrich,
Kamieth Markus,
Baumann Michael,
Wigger Arne E.,
Boese Roland,
Bläser Dieter
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200490014
Subject(s) - molecular tweezers , chemistry , naphthalene , hydroquinone , tweezers , cover (algebra) , selectivity , computational chemistry , aromaticity , force field (fiction) , stereochemistry , chemical physics , crystallography , supramolecular chemistry , crystal structure , molecule , organic chemistry , catalysis , mechanical engineering , artificial intelligence , computer science , engineering
The cover picture shows the structures of the empty dimethoxy‐substituted clip and the host−guest complex between the hydroquinone clip and 1,2,4,5‐tetracyanobenzene (TCNB) calculated by force field. The calculations are in good agreement with single‐crystal structure analyses. The compression of the naphthalene sidewalls of the clip by 2.2 A? during the complexation, which is necessary to obtain binding arene−arene interactions in the complex, is calculated to be a low‐energy process. The complementary nature of the electrostatic potential surface (EPS) of the tetramethylene‐bridged naphthalene tweezer and TCNB (calculated by AM1) explains the high selectivity of this class of receptors toward electron‐deficient substrates. Details are discussed in the article by F.‐G. Klärner et al. on p. 1405 ff. Cover art by Björn Kahlert.