Organic crystal engineering with piperazine-2,5-diones. 1. Crystal packing of piperazinediones derived from substituted 2-aminoindan-2- carboxylic acids

Lawrence J. Williams, B. Jagadish, Scott R. Lyon, Robin A. Kloster, Michael D. Carducci, Eugene A Mash

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

We have postulated that molecules engineered to participate in three chemically distinct and linearly independent intermolecular interactions will self-assemble in a predictable fashion. Six prototypes for molecules capable of manifesting such interactions were synthesized from 2-aminoindan-2- carboxylic acid, 2-amino-5,6-dimethylindan-2-carboxylic acid, and 2-amino- 4,7-dimethoxyindan-2-carboxylic acid. These piperazinediones were characterized in solution by NMR spectroscopy and in the solid state by X-ray crystallography. 'Ladder-like' intermolecular amide-to-amide hydrogen bonding interactions were observed in each case, establishing tape structures parallel to one crystallographic axis. Tape morphology varied depending on the arene substitution pattern and was governed by the development of arene and/or van der Waals contact interactions.

Original languageEnglish (US)
Pages (from-to)14281-14300
Number of pages20
JournalTetrahedron
Volume55
Issue number50
DOIs
StatePublished - Dec 10 1999

Fingerprint

Diketopiperazines
Crystal engineering
Carboxylic Acids
Amides
Tapes
Crystals
Molecules
X ray crystallography
X Ray Crystallography
Ladders
Hydrogen Bonding
Nuclear magnetic resonance spectroscopy
Hydrogen bonds
Substitution reactions
Magnetic Resonance Spectroscopy
2-aminoindan
piperazine

Keywords

  • Amino acids and derivatives
  • Indanes
  • Piperazinones
  • X-Ray crystal structures

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Organic crystal engineering with piperazine-2,5-diones. 1. Crystal packing of piperazinediones derived from substituted 2-aminoindan-2- carboxylic acids. / Williams, Lawrence J.; Jagadish, B.; Lyon, Scott R.; Kloster, Robin A.; Carducci, Michael D.; Mash, Eugene A.

In: Tetrahedron, Vol. 55, No. 50, 10.12.1999, p. 14281-14300.

Research output: Contribution to journalArticle

Williams, Lawrence J. ; Jagadish, B. ; Lyon, Scott R. ; Kloster, Robin A. ; Carducci, Michael D. ; Mash, Eugene A. / Organic crystal engineering with piperazine-2,5-diones. 1. Crystal packing of piperazinediones derived from substituted 2-aminoindan-2- carboxylic acids. In: Tetrahedron. 1999 ; Vol. 55, No. 50. pp. 14281-14300.
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AU - Kloster, Robin A.

AU - Carducci, Michael D.

AU - Mash, Eugene A

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