N-(5-nitro-2-pyrrolidinylphenyl)trifluoro-acetamide

Article abstract of DOI:10.1107/S0108270196014679

The reaction of 2-fluoro-5-nitroaniline with pyrrolidine and triethylamine in DMF gives 2-pyrrolidinyl-5-nitroaniline, and subsequent treatment with trifluoroacetic acid and thionyl chloride in DMF results in the title compound, C₁₂H₁₂F₃N₃O₃, the molecular structure of which, determined by X-ray crystallography, is described. In recent years, the interest in using organic crystals with a charge-transfer interaction via highly delocalized π-electron states (e.g. nitroanilines with donor and acceptor substituents in para positions) has increased considerably, since many of them have shown non-linear optical properties [Chemla & Zyss (1986). In Nonlinear Optical Properties of Organic Molecules and Crystals, Vols. 1 and 2. Orlando: Academic Press]. N-(5-Nitro-2-pyrrolidinylphenyl)trifluoro-acetamide (TPNB) is a donor-acceptor substituted benzene derivative and belongs to a family of compounds which produce high molecular non-linearity. TPNB shows a charge transfer (CT) between the para-disposed pyrrolidino donor and nitro acceptor groups.