Versatile inclusion behaviour of a dinitrocalix[4]arene having two ester pendants: preparation and X-ray crystal structures of complexes

Gruber, Tobias and Weber, Edwin and Seichter, Wilhelm and Bombicz, Petra and Csöregh, Ingeborg (2007) Versatile inclusion behaviour of a dinitrocalix[4]arene having two ester pendants: preparation and X-ray crystal structures of complexes. Supramolecular Chemistry, 18 (6). pp. 537-547. ISSN 1061-0278

Full text not available from this repository.

Item Type:Article
Item Status:Live Archive

Abstract

An upper-rim dinitro-substituted calix[4]arene possessing two lower-rim ethyl ester pendant groups (1) has been shown to form solid inclusion compounds with acetone (1:1) (1a), DMF (1:1) (1b), DMSO (1:1) (1c) and n-BuOH (2:1) (1d). X-ray crystal structures of the four complexes 1a–d are reported and comparatively discussed, including isostructurality calculations. Although the solid-state conformation of the dinitrocalix[4]arene moiety, stabilized by two intramolecular O–H…O bonds, is maintained in the four inclusion compounds, and all four co-crystals have similar unit cell dimensions and identical space group symmetries, only three of them (1a–c) are homostructural. Depending on the nature of the guest molecule, either the upper or the lower rim site of the calixarene is involved in the complexation, demonstrating either cavitate- or clathrate-type of supramolecular interactions, respectively. Moreover, due to the different guest recognition modes, the calixarene host in 1d is rotated through a non-crystallographic virtual rotation of 180° within the unit cell, in relation to the host molecules in each of the other three homostructural compounds 1a–c, thus giving rise to supramolecular morphotropism – to our knowledge the first case ever described.

Keywords:calixarene, inclusion compound, X-ray study, morphotropism
Subjects:F Physical Sciences > F200 Materials Science
F Physical Sciences > F160 Organic Chemistry
F Physical Sciences > F130 Structural Chemistry
Divisions:College of Science > School of Pharmacy
Related URLs:
ID Code:19717
Deposited On:01 Dec 2015 20:27

Repository Staff Only: item control page