Exploring the charge transfer dynamics of hydrogen bonded crystals of 2-methyl-8-quinolinol and chloranilic acid: synthesis, spectrophotometric, single-crystal, DFT/PCM analysis, antimicrobial, and DNA binding studies.

The new chemistry of the hydrogen-bonded charge and proton transfer complex (HB CT) between electron-donor 2-methyl-8-quinolinol (2 MQ) and electron-acceptor chloranilic acid (CHLA) has been studied using electronic absorption spectroscopy in acetonitrile (ACN), methanol (MeOH), and ethanol (EtOH) polar media at room temperature. The stoichiometric proportion of the HB CT complex was observed to be 1 : 1 from the Job data and photometric titration process. The association constant ( ) and molar absorptivity ( ) of the HB CT complex were determined by using the modified Benesi-Hildebrand equation in three polarities. Other spectroscopic physical parameters like the energy of interaction ( ), ionization potential ( ), resonance energy ( ), standard free energy change (Δ°), oscillator strength (), and transition dipole moment () were also evaluated. The HB CT complex structure was confirmed by different characterization techniques, such as FT-IR, NMR, TGA-DTA, and SEM-EDX analysis. Powder XRD and single-crystal XRD were used to determine the nature and structure of the synthesized HB CT complex. DNA binding studies for the HB CT complex produced a good binding constant value of 2.25 × 10 L mol in UV-visible and 1.17 × 10 L mol in fluorescence spectroscopy. The biological activity of the HB CT complex was also tested against the growth of bacteria and fungi, and the results indicated remarkable activity for the HB CT complex compared to the standard drugs, ampicillin and clindamycin. Hence, the abovementioned biological results of the synthesized HB CT complex show it could be used as a pharmaceutical drug in the future. Computational analysis was carried out by DFT studies using the B3LYP function with a basis set of 6-31G(d,p) in the gas phase and PCM analysis. The computational studies further supported the experimental results by confirming the charge and proton transfer complex.