Study of N-methyl-5-nitroindazolylacrylonitriles as a Function of Quantum Parameters Employing Density Function Theory Methods: Comparative Theoretical Study and Nonlinear Optical Properties

The synthesis of N-methyl-5-nitroindazolylacrylonitriles 2 a-l by a Knoevenagel condensation reaction with a series of aldehydes in the presence of piperidine allowed the preparation of the desired products the yields are good to excellent. N-Methyl-5-nitroindazolylacrylonitriles (2 a-l) were verified by H-1, C-13 NMR and mass spectrometry. In this current work, the reactivity indices defined within the Conceptual DFT of the targeted molecules through DFT/B3LYP/6-311G(d,p) calculations were studied. The H-1 NMR, UV-vis and IR spectroscopy chemical shifts of all synthesized 5-nitroindazoles 2 a-l were calculated and the results were compared to the results of the experimental data. In this series of compounds, the 2 e has the lowest hyperpolarizability, which results being the most stable and having the least response to nonlinear optics (NLO). In contrast, the compound 2 l has the highest hyperpolarizability, which fallouts being the least stable and having a high response to NLO. Every chemical has a significant three-dimensional p-electronic delocalization, which is crucial for understanding NLO responses.

Automated summary

The synthesis of N-methyl-5-nitroindazolylacrylonitriles with a series of aldehydes in the presence of piperidine yielded desired products with good to excellent yields. The synthesized compounds were confirmed by H-1, C-13 NMR and mass spectrometry. The reactivity indices of the targeted molecules were studied through DFT/B3LYP/6-311G(d,p) calculations, and the calculated spectroscopy chemical shifts were compared to experimental data. The compounds exhibited significant three-dimensional p-electronic delocalization, which is crucial for understanding their nonlinear optical responses.