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

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

doi:10.1186/s13065-019-0542-6

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.

Highlights

Thiazoles are an important class of heterocyclic compounds that possess the sulphur and nitrogen beside carbon atoms in its five member ring [1]
The natural bond orbital and molecular electrostatic potential analyses for the thiazole derivative was carried out using the B3LYP/6-311G (d, P) level [14,15,16]
Chemistry Malononitrile was stirred with phenyl isothiocyanate in potassium carbonate (K2CO3) in dimethylfluoride to afford an intermediary anionic compound 2, which on reacting with ethyl chloroacetate forming the targeted molecule 3 [9] (Fig. 1a)

Summary

Introduction

Thiazoles are an important class of heterocyclic compounds that possess the sulphur and nitrogen beside carbon atoms in its five member ring [1]. They are part of a number of pharmaceutical drugs that have analgesic (meloxicam) [2], antihistamine (nizatidine) [3], antibacterial (penicillin) [4], antifungal (thiabendazole) [5], antiprotozoal [6], and a number of other biological properties [1]. Several thiazolidine derivatives have been synthesized and their molecular structural properties have been studied both experimentally and theoretically [8]. Molecular electrostatic potential shows the reactive and non-reactive centers in the molecules while the ultra-violet visible (UV–Vis) spectrum and infra-red (IR) spectrum will be obtained from these calculations

Methods

Results

Conclusion