Unusual behavior of a calix[4]arene featuring the coexistence of basic cone and 1,2-alternate conformations in a solvated crystal

Fischer, Conrad and Gruber, Tobias and Eissmann, Diana and Seichter, Wilhelm and Weber, Edwin (2011) Unusual behavior of a calix[4]arene featuring the coexistence of basic cone and 1,2-alternate conformations in a solvated crystal. Crystal Growth & Design, 11 (5). pp. 1989-1994. ISSN 1528-7483

Full content URL: http://dx.doi.org/10.1021/cg2001877

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Unusual behavior of a calix[4]arene featuring the coexistence of basic cone and 1,2-alternate conformations in a solvated crystal

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Abstract

The X-ray crystal structure of an acetonitrile solvate of 5,11,17,23-tetra-tert-butyl-26,28-dihydroxy-25,27-dimethoxycalix[4]arene that is 1a, showing the unusual coexistence of two basic conformations in the crystal, that is, cone and 1,2-alternate, is analyzed. In contrast to this conformational coexistence of crystallographically independent molecules, the predominant conformation in solution and also in the related toluene (1b) and toluene/acetonitrile (1c) solvates is the cone conformation. With the help of calculations on the ground state energy of the single conformers and DSC measurements as well as crystallization experiments of 1 in toluene/acetonitrile mixtures of different ratio a possible explanation of this phenomenon is given.

Keywords:calixarene, cyclophane, X-ray diffraction, Molecular Conformation, Crystal engineering
Subjects:F Physical Sciences > F131 Crystallography
F Physical Sciences > F160 Organic Chemistry
F Physical Sciences > F130 Structural Chemistry
Divisions:College of Science > School of Pharmacy
ID Code:20026
Deposited On:15 Jan 2016 11:23

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