Kinetics and mechanism of acid-catalyzed hydrolysis of cyclohexyl isocyanide and pK(a) determination of N-cyclohexylnitrilium ion

Authors
Sung, KS Chen, CC
Citation
Ks. Sung et Cc. Chen, Kinetics and mechanism of acid-catalyzed hydrolysis of cyclohexyl isocyanide and pK(a) determination of N-cyclohexylnitrilium ion, TETRAHEDR L, 42(29), 2001, pp. 4845-4848
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
29
Year of publication
2001
Pages
4845 - 4848
Database
ISI
SICI code
0040-4039(20010716)42:29<4845:KAMOAH>2.0.ZU;2-W
Abstract
A novel mechanism for acid-catalyzed hydrolysis of cyclohexyl isocyanide is proposed. It is specific acid/general base catalysis, involving a fast, pr e-equilibrium C-protonation or the isocyanide, followed by a rate-determini ng attack of water on the electron-deficient carbon of the protonated isocy anide. The pK(a) of N-cyclohexylnitrilium ion was determined to be 0.86 +/- 0.05. (C) 2001 Elsevier Science Ltd. All rights reserved.