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

The Fukui function, condensed Fukui function and relative nucleophilicy ind ices DFT calculations for nitrosobenzene and 2-methyl-2-nitrosopropane nitr oso group in the gas-phase and in the water solution using SCRF SCI-PCM hav e 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, cond ensed Fukui function and relative nucleophilicity indices calculated from c harges 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, CHel p and CHelpG) emphasize the N atom as a more reactive nucleophilic site. (C ) 2001 Elsevier Science B.V. All rights reserved.