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O groups, one inward P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@cRcav 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).

Enantiospecific recognition of 2-butanol by an inherently chiral cavitand in the solid state / Brancatelli, G.; Nicosia, C.; Barboza, T.; Guy, L.; Dutasta, J. -P.; De Zorzi, R.; Demitri, N.; Dalcanale, E.; Geremia, S.; Pinalli, R.. - In: CRYSTENGCOMM. - ISSN 1466-8033. - 19:24(2017), pp. 3355-3361. [10.1039/C7CE00557A]

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

Dalcanale, E.;Pinalli, R.
2017-01-01

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O groups, one inward P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@cRcav 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).
2017
Enantiospecific recognition of 2-butanol by an inherently chiral cavitand in the solid state / Brancatelli, G.; Nicosia, C.; Barboza, T.; Guy, L.; Dutasta, J. -P.; De Zorzi, R.; Demitri, N.; Dalcanale, E.; Geremia, S.; Pinalli, R.. - In: CRYSTENGCOMM. - ISSN 1466-8033. - 19:24(2017), pp. 3355-3361. [10.1039/C7CE00557A]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2828557
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