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

Pasteur's tartaramide/malamide quasiracemates: new entries and departures from near inversion symmetry
Pasteur's tartaramide/malamide quasiracemates: new entries and departures from near inversion symmetry
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.
1466-8033
4213-4220
Pinter, Emily N.
c5c8a2b0-fe09-4ecc-8a83-1fcbbfd2f86c
Cantrell, Lee S.
c995b858-1ff2-4feb-8a9c-d1439d1b5b5b
Day, Graeme M.
e3be79ba-ad12-4461-b735-74d5c4355636
Wheeler, Kraig A.
42ed7dde-243b-484a-9f56-4a3754272f7c
Pinter, Emily N.
c5c8a2b0-fe09-4ecc-8a83-1fcbbfd2f86c
Cantrell, Lee S.
c995b858-1ff2-4feb-8a9c-d1439d1b5b5b
Day, Graeme M.
e3be79ba-ad12-4461-b735-74d5c4355636
Wheeler, Kraig A.
42ed7dde-243b-484a-9f56-4a3754272f7c

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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More information

Accepted/In Press date: 17 June 2018
e-pub ahead of print date: 22 June 2018
Published date: 2018

Identifiers

Local EPrints ID: 421742
URI: http://eprints.soton.ac.uk/id/eprint/421742
ISSN: 1466-8033
PURE UUID: 68f59270-8986-458b-a9d7-0c9d5d5bb409
ORCID for Graeme M. Day: ORCID iD orcid.org/0000-0001-8396-2771

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Date deposited: 26 Jun 2018 16:30
Last modified: 26 Nov 2021 05:03

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Contributors

Author: Emily N. Pinter
Author: Lee S. Cantrell
Author: Graeme M. Day ORCID iD
Author: Kraig A. Wheeler

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