The azatriquinenamine trimer - A novel proton chelate

Mark Mascal, Manuel Lera, Alexander J. Blake, Malgorzata Czaja, Anna Kozak, Mariusz Makowski, Lech Chmurzynski

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

A vicelike grip on a proton is exerted by the unusual nonacyclic product 1, which forms spontaneously in a unique enamine trimerization that occurs when azatriquinenamine is heated in the presence of a proton source. pKa measurements and computational modeling of the proton affinity substantiate the superbasic character of the trimer.

Original languageEnglish (US)
Pages (from-to)3696-3698
Number of pages3
JournalAngewandte Chemie - International Edition
Volume40
Issue number19
DOIs
StatePublished - Oct 1 2001

Keywords

  • Ab initio calculations
  • Enamines
  • Polycycles
  • Receptors
  • Superbases

ASJC Scopus subject areas

  • Chemistry(all)

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  • Cite this

    Mascal, M., Lera, M., Blake, A. J., Czaja, M., Kozak, A., Makowski, M., & Chmurzynski, L. (2001). The azatriquinenamine trimer - A novel proton chelate. Angewandte Chemie - International Edition, 40(19), 3696-3698. https://doi.org/10.1002/1521-3773(20011001)40:19<3696::AID-ANIE3696>3.0.CO;2-6