**Abstract**

In this work we seek to understand and to quantify the reactivity of benzofurazan derivatives toward secondary cyclic amines, like pyrrolidine, piperidine and morpholine, acting as nucleophile groups in SNAr reactions. For this aim, physico-chemical and structural descriptors were determined experimentally and theoretically using the DFT/B3LYP/6-31+ g (d,p) methodology. Thus, different 4-X-7-nitrobenzofurazans (X = OCH3, OC6H5 and Cl) and products corresponding to the electrophilic aromatic substitution by pyrrolidine, piperidine and morpholine, were investigated. Particularly, the HOMO and LUMO energy levels of the studied compounds, determined by Cyclic Voltammetry (CV) and DFT calculations, were used to evaluate the electrophilicity index (ω). The latter was exploited, according to Parr's approach, to develop a relationship which rationalizes the kinetic data previously reported for the reactions of the 4-X-7-nitrobenzofurazans with nucleophiles cited above. Moreover, the Parr's electrophilicity index (ω) of these benzofurazans determined in this work were combined with their electrophilicity parameters (E), reported in preceding papers, was found to predict the unknown electrophilicity parameters E of 4-piperidino, 4-morpholino and 4-pyrrolidino-7-nitrobenzofurazan. In addition, the relationship between the Parr's electrophilicity index (ω) and Hammett constants σ, has been used as a good model to predict the electronic effect of the nucleophile groups. Finally, we will subsequently compare the electrophilicity index (ω) and the electrophilicity parameters (E) of these series of 7-X-4-nitrobenzofurazans with the calculated dipole moment (μ) in order to elucidate general relationships between E, ω and μ.

**Keywords:** Benzofurazan, Structure–property correlations, Optical properties, Mayr's approach, Electrophilicity, Parr's approach, Voltammetry Cyclic, DFT, ICT, NLO properties
