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Synthesis and Acidity of 5-(m-Terphenyl-2'-yl)-1H-tetrazoles: Evidence for an Enhanced Polar-π Effect Compared to

Brett C Bookser1,2, Quyen-Quyen Do3, Yongsak Sritana-Anant3

  • 1Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of Medicinal Chemistry
|March 9, 2021
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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