Organic crystal engineering with 1,4-piperazine-2,5-diones. 8. Synthesis, crystal packing, and thermochemistry of piperazinediones derived from 2-amino-4,7-dialkoxyindan-2-carboxylic acids

Kirk E. Wells, Robin A. Weatherhead, Francis N. Murigi, Gary S. Nichol, Michael D. Carducci, Hugh D. Selby, Eugene A Mash

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

1,4-Piperazine-2,5-diones possessing C 2hmolecular symmetry and bearing four methoxy, ethoxy, butoxy, hexyloxy, octyloxy, nonyloxy, dodecyloxy, or octadecyloxy groups weresynthesized from 2-amino-4,7-dialkoxyindan-2- carboxylic acids. Where possible, the piperazinediones were crystallized from appropriate solvents and the supramolecular organizations were determined by X-ray crystallography. In each case so studied, crystal assembly via three mutually orthogonal interactions, namely, R22(8) hydrogen bonding, arene perpendicular edge-to-center interactions, and alkyl chain interdigitation, was observed. The thermochemical properties of these compounds were studied by modulated differential scanning calorimetry. In most cases, one or more reversible thermal events were observed between room temperature and melting to an isotropic liquid. In the cooling cycle, freezing point temperatures were observed to decrease with increasing hydrocarbon chain length. This may be due to greater entropic penalties for hydrogen-bond association of molecules with longer hydrocarbon chains.

Original languageEnglish (US)
Pages (from-to)5056-5068
Number of pages13
JournalCrystal Growth and Design
Volume12
Issue number10
DOIs
StatePublished - Oct 3 2012

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Diketopiperazines
Crystal engineering
Thermochemistry
thermochemistry
Dione
Hydrocarbons
Carboxylic Acids
Carboxylic acids
carboxylic acids
Hydrogen bonds
Bearings (structural)
hydrocarbons
engineering
thermochemical properties
Crystals
X ray crystallography
synthesis
penalties
Chain length
Freezing

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

Organic crystal engineering with 1,4-piperazine-2,5-diones. 8. Synthesis, crystal packing, and thermochemistry of piperazinediones derived from 2-amino-4,7-dialkoxyindan-2-carboxylic acids. / Wells, Kirk E.; Weatherhead, Robin A.; Murigi, Francis N.; Nichol, Gary S.; Carducci, Michael D.; Selby, Hugh D.; Mash, Eugene A.

In: Crystal Growth and Design, Vol. 12, No. 10, 03.10.2012, p. 5056-5068.

Research output: Contribution to journalArticle

Wells, Kirk E. ; Weatherhead, Robin A. ; Murigi, Francis N. ; Nichol, Gary S. ; Carducci, Michael D. ; Selby, Hugh D. ; Mash, Eugene A. / Organic crystal engineering with 1,4-piperazine-2,5-diones. 8. Synthesis, crystal packing, and thermochemistry of piperazinediones derived from 2-amino-4,7-dialkoxyindan-2-carboxylic acids. In: Crystal Growth and Design. 2012 ; Vol. 12, No. 10. pp. 5056-5068.
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