PubAg

Main content area

Endo-Complexation of Alkylammonium Ions by Calix[4]arene Cavity: Facilitating Cation−π Interactions through the Weakly Coordinating Anion Approach

Author:
Talotta, Carmen, Gaeta, Carmine, Neri, Placido
Source:
Journal of organic chemistry 2014 v.79 no.20 pp. 9842-9846
ISSN:
1520-6904
Subject:
aromatic hydrocarbons, borates, hydrogen bonding, organic chemistry, receptors
Abstract:
Notwithstanding its small dimensions, the narrow cavity of p-tert-butylcalix[4]arene macrocycle is still able to host alkylammonium guests in the presence of the tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (TFPB–) weakly coordinating (or “superweak”) anion. As an artificial analogue of biological receptors, cone-shaped calix[4]arene 1d is able to recognize a n-BuNH₃⁺ guest mainly through a 4-fold cation−π interaction aided by a weak H-bonding interaction. This recognition motif can be used to assembly a 2:1 capsular architecture with a linear diammonium axle.
Agid:
5502855