Quantum chemical approach towards the secondary amino derivatives of C(3) substituted 1,4-naphthoquinone: Combined molecular and dft calculations

Here we present molecular geometry of 2-chloro-3-(N,N-dimethyl amino)-1,4-naphthoquinone; DCDA, 2-chloro-3-(N,N-diethyl amino)-1,4-naphthoquinone; DCDA-2, 2-chloro-3-(N,N-dipropyl amino)-1,4-naphthoquinone; DCDA-3; 2-bromo-3-(N,N-dimethyl amino)-1,4-naphthoquinone; DBDA, 2-bromo-3-(N,N-diethyl amino)-1,4-naphthoquinone; DBDA-2, and 2-bromo-3-(N,N-dipropyl amino)-1,4-naphthoquinone; DBDA-3 obtained by employing density functional theory using basic functional CAM-B3LYP. Single crystal X-ray structure was solved for DCDA-2 which crystallizes in P21/n space group. Molecular frameworks are significant with hydrogen bonding interactions and were observed via. O (2)∙∙∙H (13)∙∙∙C (13), two benzenoid moiety possess π-π stacking interactions. Effect on the electro-optic behavior by halogen and aliphatic chain has been addressed by similar level of theory. Furthermore it was presumed that asymmetric polarizability induced by these investigated compounds displays enhanced non linear response and could be considered potential candidates for electro-optic and nonlinear optical applications. •Single X-ray crystal structure of 2-chloro-3(N, N-diethyl amino)-1, 4-naphthoquinone.•Intra and inter molecular hydrogen bonding.•DFT and FMO approach towards secondary amino derivatives of C (3) substituted 1,4-naphthoquinone.•Effect of halogen and extended alkyl chain on electro-optic properties.