Kinetics and mechanism of acid-catalyzed hydrolysis of cyclohexyl isocyanide and pKa determination of N-cyclohexylnitrilium ion

Kuangsen Sung, Chao Chih Chen

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A novel mechanism for acid-catalyzed hydrolysis of cyclohexyl isocyanide is proposed. It is specific acid/general base catalysis, involving a fast, pre-equilibrium C-protonation of the isocyanide, followed by a rate-determining attack of water on the electron-deficient carbon of the protonated isocyanide. The pKa of N-cyclohexylnitrilium ion was determined to be 0.86±0.05.

Original languageEnglish
Pages (from-to)4845-4848
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number29
DOIs
Publication statusPublished - 2001 Jul 16

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Kinetics and mechanism of acid-catalyzed hydrolysis of cyclohexyl isocyanide and pK<sub>a</sub> determination of N-cyclohexylnitrilium ion'. Together they form a unique fingerprint.

  • Cite this