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 Scopus citations

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

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Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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