Synthesis, spectral analysis and quantum chemical studies on molecular geometry, chemical reactivity of 7-chloro-9-(2 '-chlo rophenyl)-2,3-dihydroacridin-4(1H)-one and 7-chloro-9-(2 '-fluo rophenyl)-2,3-dihydroacridin-4(1H)-one

Abstract

7-Chloro-9-(2'-chlorophenyl)-2,3-dihydroacridin-4(1H)-one (3a) and 7-chloro-9-(2'-fluorophenyl)-2,3dihydroacridin-4-(1H)-one (3b) were synthesized from 2-amino-2',5-dichlorobenzophenone (1a) and 2-amino-5-chloro-2'-fluorobenzophenone (1b) respectively with 1,2-cyclohexanedione (2) in the presence of 1-butyl-3-methylimidazolium tetrafluoroborate and InCl3 condition. The synthesized compounds have been recorded of FT-IR, NMR spectra and the structure was further confirmed by using single crystal X-ray diffraction. The synthesized compounds have been further checked the photo physical properties like UV, emission and fluorescent quantum yields were calculated. FT-NMR spectra and H-1 and C-13 NMR chemical shifts have been measured and computational calculations of compounds 3 are done by using B3LYP method with 6-311G basis set in gas phase. Similarly calculated vibrational frequencies were found in good agreement with experimental findings. The optimized geometry of molecules 3 was compared with experimental XRD values. DFT calculations of the molecular electrostatic potential (MEP) and HOMO - LUMO frontier orbitals identified chemically active sites of compounds 3 responsible for its chemical reactivity. (C) 2016 Elsevier B.V. All rights reserved.