The crystal packing of a strongly dipolar piperazinedione

B. Jagadish, L. J. Williams, M. D. Carducci, C. Bosshard, Eugene A Mash

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A strongly dipolar piperazine-2,5-dione was synthesized in enantiomerically pure form, crystallized from DMSO, and the supramolecular organization of the crystals determined by X-ray crystallography. In contrast with non-polar or weakly polar piperazinediones of similar molecular topography, which form tapes by reciprocal intermolecular amide-to-amide hydrogen bonding, the strongly dipolar piperazinedione participated in hydrogen bonding with occluded DMSO. The dipoles of the piperazinedione molecules were aligned and were opposed by the dipoles of the DMSO molecules. The cocrystals exhibited second harmonic generation when subjected to pulsed irradiation. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)9483-9487
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number49
StatePublished - Dec 2 2000

Fingerprint

3,6-bis(5-chloro-2-piperidyl)-2,5-piperazinedione
Dimethyl Sulfoxide
Hydrogen Bonding
Amides
Crystals
Hydrogen bonds
Diketopiperazines
Molecules
X ray crystallography
X Ray Crystallography
Harmonic generation
Tapes
Topography
Irradiation

Keywords

  • Crystallization
  • Optical properties
  • Piperazinediones
  • Supramolecular chemistry
  • X-ray crystal structures

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Jagadish, B., Williams, L. J., Carducci, M. D., Bosshard, C., & Mash, E. A. (2000). The crystal packing of a strongly dipolar piperazinedione. Tetrahedron Letters, 41(49), 9483-9487.

The crystal packing of a strongly dipolar piperazinedione. / Jagadish, B.; Williams, L. J.; Carducci, M. D.; Bosshard, C.; Mash, Eugene A.

In: Tetrahedron Letters, Vol. 41, No. 49, 02.12.2000, p. 9483-9487.

Research output: Contribution to journalArticle

Jagadish, B, Williams, LJ, Carducci, MD, Bosshard, C & Mash, EA 2000, 'The crystal packing of a strongly dipolar piperazinedione', Tetrahedron Letters, vol. 41, no. 49, pp. 9483-9487.
Jagadish B, Williams LJ, Carducci MD, Bosshard C, Mash EA. The crystal packing of a strongly dipolar piperazinedione. Tetrahedron Letters. 2000 Dec 2;41(49):9483-9487.
Jagadish, B. ; Williams, L. J. ; Carducci, M. D. ; Bosshard, C. ; Mash, Eugene A. / The crystal packing of a strongly dipolar piperazinedione. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 49. pp. 9483-9487.
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