Synthesis and Structural Investigation of Some Electron-Rich Nitroaromatics

Abstract

2,4-Difluoro-, 2,4,6-Trifluoro-, and 2,3,4,6,tetrafluoronitrobenzenes undergo nucleophilic aromatic substitution, once, twice, and three times with a variety of amine substituents with a high degree of regiochemical control to provide a range of electron-rich nitrobenzene derivatives. In these structures the nitro group proves a useful structural probe to reveal the varying extents of electron donation from the varying number of amino substituents onto the nitro group as revealed by accurate low temperature X-ray crystal structure analysis, thus increasing electron donation manifests in a decrease in the Ar-NO 2 distance consistent with increased double bond character, while the N-O bond dis..