Document Type : Original Article

Authors

1 Department of Biochemistry and Molecular Biology, University of Chittagong, Chittagong,Hathazari-4334, Bangladesh

2 Chemistry, European University of Bangladesh, Dhaka, Bangladesh

3 Department of Physics, European University of Bangladesh, Dhaka-1216, Bangladesh

10.33945/SAMI/IJABBR.2020.2.2

Abstract

The morpholinium cation based ionic liquids are designed to evaluate the thermophysical, chemical reactivity, and biological activity. To estimate and design the bioactive ILs, propionate and trihalopropanoate were considered under theoretical study by Density Functional Theory (DFT). To make effect of halogens atom on anion, propionate, trifluro propionate, trichloro propionate, and tribromo propionate were taken for optimization. Some thermodynamic and thermophysical properties such as free energy, entropy, dipole moment, binding energy, nuclear energy, electronics energy, and heat of formation were calculated using DFT method and make a comparative effect for halogen atoms activity on anion. The free energy, binding energy, and heat of formation were the highest on morphonium trifluro propionate (IL02) and the second is on tribromo propionate (IL04). Quantitative Structure Activity Relationship (QSAR) like charge density, surface area grid, volume, LogP, polarizability, refractivity, and molecular mass were simulated and recorded, from which the biological activity was calculated. The chemical reactivity like HOMO, LUMO, HOMO-LUMO gap, ionization potential, hardness, softness electronegativity and electron affinity were calculated. The vibrational spectroscopy and UV spectroscopy data provide them the identification and characterization. To sum up, the thermophysical properties are highly affected by trifluro propionate anion then tribromo propionate, trichloro propionate, and propionate respectively. On the other hand, the chemical reactivity increases in order IL04, IL03, IL02, IL01 but biological activity is inversely changed.

Keywords

Böhm, M, St rzebecher, J, Klebe, G. (1999). Three-dimensional quantitative structure− activity relationship analyses using comparative molecular field analysis and comparative molecular similarity indices analysis to elucidate selectivity differences of inhibitors binding to trypsin, thrombin, and factor Xa. J. Med. Chem., 42(3):458-477.
Canadell, ER, Ravy, S, Pouget, JP, Brossard, L. (1990). Concerning the band structure of D (M (dmit) 2) 2 (D= TTF, Cs, NMe4); M= Ni, Pd) molecular conductors and superconductors: Role of the M (dmit) 2 Homo and Lumo. Solid State Commun., 75(8):633-638.
Collins, KD. (1997). Charge density-dependent strength of hydration and biological structure. Biophys. J., 72(1):65-76.
Freitas, VL, Gomes, JRB, Ribeiro da Silva, MDMC. (2014). Energetics and reactivity of morpholine and thiomorpholine: a joint experimental and computational study. J. Chem. Eng. Data, 59(2):312-322.
Grotenbreg, GM, Christina, AE, Buizert, AE, van der Marel, GA, Overkleeft, HS, Overhand, M. (2004). Synthesis and application of carbohydrate-derived morpholine amino acids. J. Org. Chem., 69(24):8331-8339.
Hossain, MI, Kumer, A. (2017). Synthesis and characterization of ammonium benzilate bioactive ionic liquids and their antimicrobial activity. Asian J. Phys. Chem. Sci., 4(4):1-13.
Hossain, MI, Kumer, A. (2017). Synthesis and Characterization of Ammonium Ionic Liquids and Their Antimicrobial and Computational Overview. Asian J. Phys. Chem. Sci., 3(4):1-10.
Hossain, MI, Kumer, A. (2017). Synthesis and characterization of ammonium benzilate bioactive ionic liquids and their antimicrobial activity. Asian J. Phys. Chem. Sci., 4(4):1-13.
Hossain, MI, Kumer, A. Begum, S. (2018). Synthesis and Characterization of Ammonium Benzoate and Its Derivative Based Ionic Liquids and Their Antimicrobial Studies. Asian J. Phys. Chem. Sci., 5(1):1-9.
Hossain, MI, El-Harbawi, M, Kumer, A. (2015). Acute toxicity of OH functionalized ionic liquids to the aquatic species. Int. J. Adv. Eng. Sci. Technol., (IJAEST), 4(3):244-249.
Howard, A, J. McIver, et al. (1994). Hyperchem computational chemistry. Hypercube Inc., Waterloo.
Islam, MJ,  Kumer, A, Sarker, N, Paul, S, Zannat, A. (2019). The prediction and theoretical study for chemical reactivity, thermophysical and biological activity of morpholinium nitrate and nitrite ionic liquid crystals: A DFT study. Adv. J. Chem. Section A, 2(4):316-326.
Islam, MJ, Sarker, N, Kumer, A, Paul, S. (2019). The Evaluation and Comparison of Thermo-Physical, Chemical and Biological Properties of Palladium(II) Complexes on Binuclear Amine Ligands with Different Anions by DFT Study. Int. J. Adv. Biol. Biomed. Res., 7(4):15-334.
Izquierdo, I. (1979). Effect of naloxone and morphine on various forms of memory in the rat: Possible role of endogenous opiate mechanisms in memory consolidation. Psychopharmacology, 66(2):199-203.
Koopmans, YT. (1934). Uber die zuordnung von wellenfunktionen und eigenwerten zu den,einzelnen elektronen eines atoms. Physica, 1(1-6):104-113.
Kumer, A, Ahmed, B, Sharif, A, Al-Mamun, A. (2017). A Theoretical Study of Aniline and Nitrobenzene by Computational Overview. Asian J. phys. Chem. Sci., 4(2):1-12.
Kumer, A, Sarker, N, Paul, S. (2019). The Simulating Study of HOMO, LUMO, thermo physical and Quantitative Structure of Activity Relationship (QSAR) of Some Anticancer Active Ionic Liquids. Eurasian J. Environ. Res., 3(3):1-10.
Kumer, A, Sarker, N, Paul, S. (2019). The thermo physical, HOMO, LUMO, Vibrational spectroscopy and QSAR study of morphonium formate and acetate Ionic Liquid Salts using computational method. Turkish Computat. Theoret. Chem., 3(2):59-68.
Kumer, A, Sarker, N, Paul, S. (2019). The Theoretical Prediction of Thermophysical properties, HOMO, LUMO, QSAR and Biological Indics of Cannabinoids (CBD) and Tetrahhdrocannabinol (THC) by Computational Chemistry. Adv. J. Chem. Section A, 2(3):190-202.
Kumer, A, Sarker, N, Paul, S. (2019). The theoretical investigation of HOMO, LUMO, thermophysical properties and QSAR study of some aromatic carboxylic acids using HyperChem programming. Int. J. Chem. Technol., 3(1):26-37.
Kumer, A, Sarker, N, Paul, S. Afroza Z. (2019). The Theoretical Prediction of Thermophysical properties, HOMO, LUMO, QSAR and Biological Indics of Cannabinoids (CBD) and Tetrahhdrocannabinol (THC) by Computational Chemistry. Adv. J. Chem., 3(3):1-13.
Kumer, A, Sarker, N, Paul, S. (2019). The theoretical investigation of HOMO, LUMO, thermophysical properties and QSAR study of some aromatic carboxylic acids using HyperChem programming. Int. J. Chem. Technol., 3(1):26-23.
Lanman, BA, Myers, AG. (2004). Efficient, stereoselective synthesis of trans-2, 5-disubstituted morpholines. Org. Lett., 6(6):1045-1047.
Martini, L, Whistler, JL. (2007). The role of mu opioid receptor desensitization and endocytosis in morphine tolerance and dependence. Current Opin. Neurobiol., 17(5):556-564.
Newington, I, Perez-Arlandis, JM, Welton, T. (2007). Ionic liquids as designer solvents for nucleophilic aromatic substitutions. Org. Lett., 9(25):5247-5250.
Timofeeva, L, Kleshcheva, N. (2011). Antimicrobial polymers: mechanism of action, factors of activity, and applications. Appl. Microbial. Biotechnol., 89(3):475-492.
Wang, XS, Tabor, MW. (1988). Studies of the reactivity of morpholine, 2‐mercaptobenzothiazole and 2 of their derivatives with selected amino acids. Contact Dermatitis., 19(1):16-21.