In this study, 5,6-dihydro-11H-benzo[α]carbazole (BDHC) with electron-withdrawing, 1(a-h)-5(a-h) and donating, 6(a-h)-10(a-h) substituents were performed at B3LYP/6-31G* level of theory. BDHC and its derivatives with chemical and biochemical activities are described in terms of various quantum chemical descriptors which are the global hardness (η), the chemical potential (μ), electrophilicity index (ω) and dipole moment (DM). For electron-withdrawing groups, 1(a-h)-5(a-h) on A and D rings of BDHC, it is proven that electrophilicity index, the chemical potential and the global hardness sequences are consistence within each other, but DM values of 1(a-h)-5(a-h) do not. In contrast, the substitution at a-h positions of BDHC with electron-donating groups, 6(a-h)-10(a-h) do not display an enourmous diversity in all calculated quantum chemical descriptors, according to all electron-withdrawing groups, 1(a-h)-5(a-h). As seen at the chemical descriptors, it is found that -OCH3(in c-position on A ring) and -OH (in g-position on D ring) are most effective structures. According to these calculations, we conclude that the most probable predicted biochemicaly active structures are -NO2substituent (in d- and f-position on A and D rings) among electron-withdrawing groups and -OCH3(in c-position on A ring), -OH (in h-position on D ring) substituents among electron-donating groups. According to the calculated molecular electron density of BDHC and its derivatives, c- and d-positions on A ring and e- and f-positions on D ring are more effective on electron-withdrawing and -donating substituted structures, so different substituents 1(a-h)-10(a-h) do not also have any distinct effect on charge distributions of BDHC derivatives. © 2006 Elsevier B.V. All rights reserved.
Taskin, T., & Sevin, F. (2007). Theoretical investigation on chemical and biochemical activities of 5,6-dihydro-11H-benzo[α]carbazole and its derivatives. Journal of Molecular Structure: THEOCHEM, 803(1–3), 61–66. https://doi.org/10.1016/j.theochem.2006.09.028