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Issue 40, 2012
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The origin of isotope-induced helical-sense bias in supramolecular polymers of benzene-1,3,5-tricarboxamides

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Abstract

The molecular origin of the isotope-induced diastereomeric enrichment in helical supramolecular polymers consisting of trialkylbenzene-1,3,5-tricarboxamides (BTAs) is studied using plane-wave DFT calculations. We demonstrate that the creation of a chiral center at the α-position of the alkyl chains of a BTA by H–D exchange leads to a small but notable preference for the formation of supramolecular hydrogen bonded structures with a particular helicity. The bias for one helical sense preference is caused by the orientation of the vibrational eigenmodes of the C–H and C–D stretching frequencies at the chiral center and by hyperconjugative destabilization of the anti C–H orbital.

Graphical abstract: The origin of isotope-induced helical-sense bias in supramolecular polymers of benzene-1,3,5-tricarboxamides

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The article was received on 06 Jul 2012, accepted on 16 Aug 2012 and first published on 17 Aug 2012


Article type: Paper
DOI: 10.1039/C2CP42302B
Citation: Phys. Chem. Chem. Phys., 2012,14, 13997-14002
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    The origin of isotope-induced helical-sense bias in supramolecular polymers of benzene-1,3,5-tricarboxamides

    I. A. W. Filot, A. R. A. Palmans, P. A. J. Hilbers, E. J. M. Hensen, T. F. A. de Greef and E. A. Pidko, Phys. Chem. Chem. Phys., 2012, 14, 13997
    DOI: 10.1039/C2CP42302B

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