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Why is tetrazole formation by addition of azide to organic nitriles catalyzed by zinc(II) salts?

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Overview

related to degree

  • Demko, Zachary, Ph.D. in Chemistry, Scripps Research 1997 - 2002

authors

  • Himo, F.
  • Demko, Zachary
  • Noodleman, Louis
  • Sharpless, K. Barry

publication date

  • 2003

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The mechanism by which zinc(II) catalyzes the union of an azide ion with organic nitriles to form tetrazoles is investigated by means of density functional theory using the hybrid functional B3LYP. The calculations indicate that coordination of the nitrile to the zinc ion is the dominant factor affecting the catalysis; this coordination substantially lowers the barrier for nucleophilic attack by azide. Relative reaction rates of catalyzed and uncatalyzed tetrazole formation also provide experimental support for this conclusion.

subject areas

  • Azides
  • Catalysis
  • Cyclization
  • Models, Molecular
  • Nitriles
  • Tetrazoles
  • Zinc
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja030204q

PubMed ID

  • 12914461
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Additional Document Info

start page

  • 9983

end page

  • 9987

volume

  • 125

issue

  • 33

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