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Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles

Floris Chevallier1, Thomas Blin, Elisabeth Nagaradja

  • 1Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS- Université de Rennes 1, Bâtiment 10A, Case 1003, Campus Scientifique de Beaulieu, 35042 Rennes, France. floris.chevallier@univ-rennes1.fr

Organic & Biomolecular Chemistry
|May 22, 2012
PubMed

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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
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