Abstract
It is shown by use of the method of Fourier transform ion cyclotron resonance mass spectrometry that imidate anions, generated by deprotonation of formamide, acetamide, N-methylformamide and trifluoroacetamide, exhibit an ambident chemical behavior in their gas-phase reactions with unsaturated perfluorocarbon compounds. This ambident behavior implies a competition between addition via the nitrogen and oxygen nucleophilic centers and appears to parallel the previously-studied ambident behavior of enolate anions in the gas phase. Rationalization of the selectivity of the studied imidate anion reactions has been discussed in terms of electrostatic and specific orbital interactions in the reaction complex. Likewise, thio-imidate anions generated by deprotonation of thioacetamide show an ambident chemical behavior which allows a fair competition between addition via the nitrogen and sulfur nucleophilic centers in the gas-phase reactions with unsaturated perfluorocarbon compounds.
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: International Journal of Mass Spectrometry and Ion Processes
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.
