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

Pinter, Emily N., Cantrell, Lee S., Day, Graeme M. and Wheeler, Kraig A. (2018) Pasteur's tartaramide/malamide quasiracemates: new entries and departures from near inversion symmetry. CrystEngComm, 20 (30), 4213-4220. (doi:10.1039/c8ce00791h).

Record type: Article

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 theory functional calculations were applied to quantify the crystal stabilization and rationalize the observed packing tendencies.

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