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Related Experiment Videos

Connectivity effects in isomeric naphthalenedinitrenes.

P R Serwinski1, R Walton, J A Sanborn

  • 1Department of Chemistry, University of Massachusetts, Amherst, Massachusetts 01003, USA.

Organic Letters
|June 29, 2001
PubMed
Summary
This summary is machine-generated.

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Photolysis of naphthalenediazides at cryogenic temperatures produced mononitrenes and diiminediyls. Spectroscopic and computational data suggest quinonoidal singlet structures for diiminediyls, not aromatic dinitrenes.

Area of Science:

  • Photochemistry
  • Spectroscopy
  • Computational Chemistry

Background:

  • Naphthalenediazides are precursors to reactive nitrogen species.
  • Understanding the structure of photolysis products is crucial for reaction mechanism elucidation.

Purpose of the Study:

  • To investigate the photolysis products of 1,4- and 1,5-naphthalenediazide.
  • To determine the ground-state structures of the resulting diiminediyl species.

Main Methods:

  • UV-vis, FTIR, and ESR spectroscopy.
  • Photolysis at cryogenic temperatures in argon and frozen solvent matrices.
  • Computational analysis.

Main Results:

  • Photolysis yielded mononitrene and diiminediyl intermediates.

Related Experiment Videos

  • Spectroscopic and computational data support quinonoidal singlet structures for diiminediyls.
  • Aromatic dinitrene structures were inconsistent with the findings.

    • Conclusions:

    • The photolysis of naphthalenediazides leads to quinonoidal diiminediyls.
    • This study clarifies the structural properties of these transient species.