Computational studies of 2-(4-oxo-3-phenylthiazolidin-2-ylidene)malononitrile

Yahia N Mabkhot; Salim S Al-Showiman; A Barakat; S M Soliman; Nabila A Kheder; Mohammed M Alharbi; Abdulrahman Asayari; Abdullatif Bin Muhsinah; Asad Ullah; Syed Lal Badshah

doi:10.1186/s13065-019-0542-6

Computational studies of 2-(4-oxo-3-phenylthiazolidin-2-ylidene)malononitrile

BMC Chem. 2019 Feb 18;13(1):25. doi: 10.1186/s13065-019-0542-6. eCollection 2019 Dec.

Authors

Affiliations

¹ 1Department of Pharmaceutical Chemistry, College of Pharmacy, King Khalid University, Abha, 61441 Saudi Arabia.
² 2Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh, 11451 Saudi Arabia.
³ 3Department of Chemistry, Faculty of Science, Alexandria University, P.O Box 426, Ibrahimia Alexandria, 21321 Egypt.
⁴ 4Department of Chemistry, Rabigh College of Science and Art, King Abdulaziz University, Jeddah, 21589 Saudi Arabia.
⁵ 5Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613 Egypt.
⁶ 6Department of Pharmacognosy, College of Pharmacy, King Khalid University, Abha, 61441 Saudi Arabia.
⁷ 7Department of Chemistry, Islamia College University Peshawar, Peshawar, 25120 KPK Pakistan.

Abstract

The molecular structure of the 2-(4-oxo-3-phenylthiazolidin-2-ylidene) malononitrile (3) is calculated using DFT B3LYP/6-311G(d, p) method. The calculated geometric parameters are in good agreement with the experimental data. The NBO calculations were performed to predict the natural atomic charges at the different atomic sites and study the different intramolecular charge transfer (ICT) interactions occurring in the studied system. The BD(2)C17-C19 → BD*(2)C14-C15, LP(2)O2 → BD*(1)N5-C9 and LP(1)N5 → BD*(2)C10-C11 ICT interactions causing stabilization of the system by 23.30, 30.63 and 52.48 kcal/mol, respectively. The two intense electronic transition bands observed experimentally at 249 nm and 296 nm are predicted using the TD-DFT calculations at 237.9 nm (f = 0.1618) and 276.4 nm (f = 0.3408), respectively. These electronic transitions are due to H-3 → L (94%) and H → L (95%) excitations, respectively.

Keywords: DFT/B3LYP calculations; Molecular docking; NBO calculations; Thiazole.