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Issue 30, 2018
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Pasteur's tartaramide/malamide quasiracemates: new entries and departures from near inversion symmetry

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Abstract

This investigation explores Pasteur's 1853 (+)-tartaramide/(−)-malamide quasiracemate, extends this system to the crystallization behavior of methyl and butyl derivatives, and challenges the well-known notion that pairs of quasienantiomers assemble without exception to give near centrosymmetric crystal packing motifs. Each of the structures included in this study exhibits an extensive set of N/O–H⋯O contacts with component alignment in the quasiracemates defined by inversion and/or glide symmetry. Solid-state density functional theory calculations were applied to quantify the crystal stabilization and rationalize the observed packing tendencies.

Graphical abstract: Pasteur's tartaramide/malamide quasiracemates: new entries and departures from near inversion symmetry

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Publication details

The article was received on 14 May 2018, accepted on 17 Jun 2018 and first published on 22 Jun 2018


Article type: Communication
DOI: 10.1039/C8CE00791H
Citation: CrystEngComm, 2018,20, 4213-4220
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    Pasteur's tartaramide/malamide quasiracemates: new entries and departures from near inversion symmetry

    E. N. Pinter, L. S. Cantrell, G. M. Day and K. A. Wheeler, CrystEngComm, 2018, 20, 4213
    DOI: 10.1039/C8CE00791H

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