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Kinetic and equilibrium lithium acidities of arenes: theory and experiment

Andrew Streitwieser1, Kamesh Shah, Julius R Reyes

  • 1Department of Chemistry, University of California-Berkeley, Berkeley, California 94720-1460, USA. astreit@berkeley.edu

The Journal of Physical Chemistry. A
|May 14, 2010
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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