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Alkylammonium Guest Induced‐Fit Recognition by a Flexible Dihomooxacalix[4]arene Derivative
Author(s) -
Talotta Carmen,
Gaeta Carmine,
De Rosa Margherita,
Ascenso José R.,
Marcos Paula M.,
Neri Placido
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501319
Subject(s) - chemistry , derivative (finance) , stereochemistry , ammonium , molecular recognition , molecule , organic chemistry , financial economics , economics
The conformationally mobile tetramethoxy‐dihomooxacalix[4]arene 1c is able to interact with linear and branched alkylammonium guests through an induced‐fit process mainly driven by H‐bonds and cation–π interactions. Although free 1c adopts a 1,4‐alternate conformation in solution, in the presence of linear n BuNH 3 + and branched s BuNH 3 + and i PrNH 3 + guests, it preferentially forms endo ‐complexes in a cone conformation through adaptive structural change in response to the presence of the ammonium guests. In accordance with previous results, the DFT‐optimized structures of the complexes indicate that they are mainly stabilized by H‐bonding interactions between the guest ammonium group and the host CH 2 OCH 2 ethereal bridge.