Synthesis, structure investigation, DFT analysis, optical, and photoelectrical properties of 9-bromo-3-hydroxychromeno[4,3-b]pyrazolo[4,3-e]pyridin-5(1H)-one (BHCPP)

Abstract

Chemical transformation of 6-bromochromone-3-carbonitrile (1) with cyanoacetohydrazide in boiling acetic acid yielded the novel 9-bromo-3 hydroxychromeno[4,3-b]pyrazolo[4,3-e]pyridin-5(1H)-one (2, BHCPP). At the B3LYP/6–311++G (d, p) level, Density Functional Theory (DFT) and Time-Dependent DFT (TD-DFT) were utilized to investigate optimal geometry, natural bond orbital (NBO) analyses, FT-IR spectroscopic data, frontier molecular orbitals (FMOs), perpendicular electronic transition states, and NLO characteristics. The calculated total energy and thermodynamic characteristics at the same level of calculations confirmed the higher stability of the suggested structure (BHCPP) as compared with other predictable products (C, D and 3). DFT computed results and the associated experimental data were found to be in good agreement. The alpha pyrone derivative (BHCPP) was discovered to be the most stable structure in both the gaseous and solution states using PCM. The calculated total energies of all expected products are increase in solution, indicating solvent stabilizes all predicted products. Based on the experimental and theoretical results, the synthetic pathway for the formation of compound 3 was excluded, while compounds C and D considered as intermediates throughout the preparation of the more stable product 2 (BHCPP). The global reactivity descriptors were calculated using the energy of FMOs, indicating the molecule is chemically hard with increased kinetic stability and electron donating capabilities. The antimicrobial investigation was examined for the prepared compound (BHCPP).