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Issue 24, 2017
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Enantiospecific recognition of 2-butanol by an inherently chiral cavitand in the solid state

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Abstract

A new inherently chiral cavitand is described, in which the desymmetrization of the rigid concave cavity is achieved by introducing three different bridging groups at the upper rim, namely two inward P[double bond, length as m-dash]O groups, one inward P[double bond, length as m-dash]S moiety and one methylene bridge in the AABC mode. The racemic mixture of cR and cS enantiomers is resolved by semi-preparative chiral HPLC and the enantiopurity confirmed through circular dichroism. The properties of the enantiopure cR-cav in the enantioselective recognition of racemic 2-butanol is studied by co-crystallization experiments. The exclusive formation of the complex R-BuOH@cR-cav demonstrates that cR-cav is able to discriminate between the two enantiomers of the alcohol in the solid state. The enantiospecific recognition exhibited by the cR-cav towards racemic 2-butanol is particularly relevant because of the low degree of chirality of the alcohol (1.9 calculated by CCM algorithm).

Graphical abstract: Enantiospecific recognition of 2-butanol by an inherently chiral cavitand in the solid state

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Publication details

The article was received on 23 Mar 2017, accepted on 26 May 2017 and first published on 26 May 2017


Article type: Paper
DOI: 10.1039/C7CE00557A
Citation: CrystEngComm, 2017,19, 3355-3361
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    Enantiospecific recognition of 2-butanol by an inherently chiral cavitand in the solid state

    G. Brancatelli, C. Nicosia, T. Barboza, L. Guy, J.-P. Dutasta, R. De Zorzi, N. Demitri, E. Dalcanale, S. Geremia and R. Pinalli, CrystEngComm, 2017, 19, 3355
    DOI: 10.1039/C7CE00557A

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