Abstract
The hydrolysis of phenyl isocyanate is subject to general base catalysis by tertiary amines and the point for water falls on the Bronsted plot, which indicates that the uncatalysed reaction involves two molecules of water, one acting as a nucleophile and the other as a general base. The rather small solvent isotope effect, kwH2O/kwD2O= 1.65, and the proton inventory, are discussed. The hydrolysis of methyl isocyanate (unlike phenyl isocyanate) is acid- catalysed, probably proceeding with pre-equilibrium protonation. Methyl isocyanate reacts with hydrogenphosphate dianion and with hydrogensulphate ion, forming mixed anhydride species. The formal reaction with hydrogensulphate ion may proceed by pre-equilibrium protonation followed by nucleophilic attack by sulphate ion.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
