Nucleophilic reactivity of the nitroso group. Fukui function DFT calculations for nitrosobenzene and 2-methyl-2-nitrosopropane

Abstract

The Fukui function, condensed Fukui function and relative nucleophilicy indices DFT calculations for nitrosobenzene and 2-methyl-2-nitrosopropane nitroso group in the gas-phase and in the water solution using SCRF SCI-PCM have been presented and discussed. Considering the calculated Fukui functions, both the N and the O atomic centres are found to be suitable nucleophilic reactive sites in the gas-phase and in the water solution. Condensed Fukui function and relative nucleophilicity indices support this view. Also, condensed Fukui function and relative nucleophilicity indices calculated from charges obtained with orbital charge calculation methods (MPA and NPA) show that the O atom of the nitroso group is a more reactive nucleophilic centre, while indices derived from the electrostatic potential charges (MKS, CHelp and CHelpG) emphasize the N atom as a more reactive nucleophilic site.