DFT quantum chemical calculations and statistical analysis of 2-amino-6-arylsulfonylbenzonitrile derivatives and their electrical properties

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Yılmazer M. İ., Saraçoğlu M., Başaran M. A., Sayiner H. S., Kandemirli F.

JOURNAL OF CHEMICAL SOCIETY OF PAKISTAN, cilt.48, sa.1, 2026 (SCI-Expanded, Scopus)

• Yayın Türü: Makale / Tam Makale
• Cilt numarası: 48 Sayı: 1
• Basım Tarihi: 2026
• Dergi Adı: JOURNAL OF CHEMICAL SOCIETY OF PAKISTAN
• Derginin Tarandığı İndeksler: Scopus, Science Citation Index Expanded (SCI-EXPANDED), Chemical Abstracts Core
• Erciyes Üniversitesi Adresli: Evet

Özet

Quantum chemical calculations were performed for gas and water phases using the DFT/B3LYP/6-311G(d,p) basis set to determine some molecular properties of 2-amino-6-arylsulfonylbenzonitrile derivatives (1-61). The quantum chemical properties of these compounds such as E_HOMO (highest occupied molecular orbital energy), E_LUMO (lowest unoccupied molecular orbital energy), HOMO-LUMO energy gap (∆E), ionization potential (I), chemical hardness (η) and softness (σ), etc. values were calculated and the results were discussed. This research aims to construct the relationship between HIV-reverse transcriptase inhibitory activity (pIC₅₀) values and classical-quantum descriptors (attributes) of 61 compounds. The values of the attributes are extracted by utilizing B3LYP/6-311G(d,p) method. This endeavour leads to different statistical models since the data contain both nonlinearity and clustered structure. In this study, 2-amino-6-arylsulfonylbenzonitrile derivatives (1-61) were classified into three subsets based on the atom or group attached at the X position: Subset S (compounds 1-19), Subset SO (compounds 20-32), and Subset SO₂ (compounds 33-61). Then each subgroup is split into more statistically homogeneous subsets using statistical models suggesting that the ratio denoted by is the most significant variable that accounts for pIC₅₀ for both groups of S and SO₂ with 95 and 90 percent coefficients of determination, respectively. On the other hand, for the group SO, we have a more complicated significant variable that accounts for pIC₅₀, which is .

Moreover, In the context of 2-amino-6-arylsulfonylbenzonitrile derivatives, compounds 2, 24, and 50 for gas phase, and compounds 15, 30, and 50 for water phase exhibit higher HOMO energies and smaller ΔE values compared to other molecules in the series. This suggests that, according to the ΔE values, these compounds have a higher tendency to donate electrons and have a more effective reactivity than the other compounds in the series.