Spectroscopic and theoretical studies on the nucleophilic substitution of 2,3-dichloronaphthoquinone with para-substituted anilines in solid state via initial charge transfer complexation

Various spectroscopy techniques (UV–Vis, DRS, FT-IR, 1H NMR, LC–MS) and theoretical computations have been employed to investigate the mechanism of the nucleophilic substitution reaction of 2,3-dichloronaphthoquinone (DCNQ) with para-substituted anilines in solid state under base- and solvent-free conditions against traditional synthetic routes. The initial formations of electron donor acceptor (EDA) adduct between DCNQ and aniline was found to be the driving force for the substitution reaction to occur in solid phase.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Nucleophilic substitution of DCNQ with anilines in solid state has been demonstrated. ► Driving force for the reaction is the ease with which initial EDA adduct forms between reactants. ► It is an environment friendly attempt for the preparation of aminonaphthoquinone derivatives.