Investigation of the effect of non-covalent interactions on the structure of 1,2,4-triazole-3-thione and acylhydrazone compounds by the nmr spectroscopy

Tetrahydrocarbazoles and carbazoles have become preferred compounds due to their electronic properties, chemical stability, the ability to be derivatized with functional groups, and high photophysical properties. Thanks to these properties, they have a wide range of applications in organic electronics, chemical sensors, pharmaceutical applications, and materials science. Acylhydrazones and 1,2,4-triazole-3-thione compounds with electrophilic and nucleophilic centers, great structural diversity, and high possibilities for modification represent another important class of compounds. Because of their biological activities, complexation abilities, chemical durability, and biological properties, these compounds are preferred in pharmaceutical applications, chemical sensors, catalysis, and advanced materials. Due to the growing importance of hybrid compounds based on carbazole and tetrahydrocarbazole structures in recent years, in both materials science and pharmaceutical science, these compounds have become an interesting target for synthetic organic chemists. The easy and efficient synthesis and structural characterization of such hybrid compounds contributes to scientific literature and industrial applications. These unique properties of these compounds open the door to discoveries and innovations in disciplines such as medicine and materials science, thus encouraging major advances. Continuing research on these compounds is significant for all scientists. For this purpose, this thesis synthesizes acylhydrazone and 1,2,4-triazole-3-thione derivatives based on tetrahydrocarbazole and carbazole core structures. In the first part of the thesis, 19 novel tetrahydrocarbazole-based 1,2,4-triazole-3-thione derivatives (41-59) were synthesized, purified, and then characterized by spectroscopic techniques including 1H NMR, 13C NMR, MS, and FT-IR. The intramolecular non-covalent interactions of the synthesized compounds have been probed using 1H and 13C NMR techniques, and their dimensional structures have been elucidated without resorting to more sophisticated spectroscopic techniques. In the second part of the thesis, for structural investigations, 11 acylhydrazone derivatives (60-67 and 70-72) with tetrahydrocarbazole and carbazole structures were synthesized. These compounds were purified and characterized by FT-IR, MS, 1H NMR, and 13C NMR spectroscopy. The tautomers and isomers of the acyl hydrazone compounds were investigated by 1H, 13C, COSY, and NOESY NMR techniques.