Crystal structure of 4,4′-bis[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphenyl-Walbaum Anqi

Anqi Walbaum, E. Kim Fifer, Sean Parkin, Peter A. Crooks

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The title compound, C28H32N2, (I), is one of a second generation of compounds designed and synthesized based on a very potent and selective α9α10 nicotinic acetylcholine receptor antagonist ZZ161C {1,1′-[[1,1′-biphenyl]-4,4′-diylbis(prop-2-yne-3,1-diyl)]bis(3,4-dimethylpyridin-1-ium) bromide}, which has shown analgesic effects in a chemotherapy-induced neuropathy animal model. Compound (I) was synthesized by the reaction of 4,4′-bis(3-bromoprop-1-yn-1-yl)-1,1′-biphenyl with piperidine at room temperature in acetonitrile. The single-crystal used for X-ray analysis was obtained by dissolving (I) in a mixture of dichloromethane and methanol, followed by slow evaporation of the solvent. In the crystal of (I), the biphenyl moiety has a twisted conformation, with a dihedral angle of 25.93 (4)° between the benzene rings. Both piperidine head groups in (I) are in the chair conformation and are oriented so that the N-Atom lone pairs of each piperidine group point away from the central biphenyl moiety.

Original languageEnglish
Pages (from-to)864-866
Number of pages3
JournalActa Crystallographica Section E: Crystallographic Communications
Volume73
DOIs
StatePublished - 2017

Bibliographical note

Funding Information:
This investigation was supported by the Arkansas Research Alliance (ARA)

Publisher Copyright:
© 2017.

Keywords

  • biphenyl system
  • bis-Tertiary ammonium salt
  • crystal structure
  • piperidine ring

ASJC Scopus subject areas

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

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