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Amidine nitrosation.

Richard N Loeppky1, Hongbin Yu

  • 1Department of Chemistry, University of Missouri-Columbia, Columbia, Missouri 65211, USA. loeppkyr@missouri.edu

The Journal of Organic Chemistry
|April 24, 2004
PubMed
Summary
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This study investigated the acidic nitrosation of amidines, finding that amides and diazonium ions are primary products. Tertiary amidines also yielded nitrosamines, with pyrrolidine-derived amidines showing the highest reactivity.

Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms
  • Nitrosation Chemistry

Background:

  • Amidine chemistry is crucial in organic synthesis and medicinal chemistry.
  • Understanding nitrosation reactions is vital for assessing potential risks and developing new synthetic pathways.

Purpose of the Study:

  • To investigate the acidic nitrosation chemistry of various acyclic secondary and tertiary amidines and N-acylamidines.
  • To elucidate the reaction mechanism, identify principal products, and determine rate constants.

Main Methods:

  • Acidic nitrosation of nine acyclic amidines and several N-acylamidines using excess nitrite in aqueous acetic acid at 25°C.
  • Quantitation of reaction products, including amides, diazonium ions, and nitrosamines.
  • Measurement of pseudo-first-order rate constants and determination of amidine basicity (pKa).

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Main Results:

  • Principal nitrosation products were amides and compounds derived from benzenediazonium ion.
  • Tertiary amidines yielded minor but significant amounts of nitrosamines.
  • Benzamidines showed no reactivity, and N-acylamidines hydrolyzed rapidly.
  • Pyrrolidine-derived amidines were the most reactive when corrected for basicity.
  • Rate constants ranged from (3 to 106) x 10(-5) s(-1) over a 5 pKa unit range.

Conclusions:

  • The reaction proceeds via nitrosation on the imino nitrogen, followed by water addition and decomposition to amides and diazonium ions.
  • A significant pathway for pyrrolidine-derived amidines involves cleavage and nitrosation to form N-nitrosopyrrolidine.
  • The lack of benzamidine reactivity is due to slow water addition and reversible nitrosation.