DFT/TD-DFT ANALYSIS OF 2-CHLORO-7-METHYLQUINOLINE-3-CARBALDEHYDE USING COMPUTER COMPUTING METHOD

Yıl 2021, Cilt: 9 Sayı: Iconat Special Issue 2021, 85 - 93, 24.12.2021

Nihal Kuş

https://doi.org/10.20290/estubtdb.1015151

Öz

Quinolines are the essence of many natural products, drugs and were found in synthetic compounds. Quinoline derivatives containing a quinoline ring are used in a variety of biological and pharmaceutical activities, e.g. anticancer, antibacterial, antifungal, antiplasmodial, antihistamine, antimalarial and antituberculosis. In this study, 2-Chloro-7-Methylquinoline-3-Carbaldehyde (ClMQC) molecule, which is a quinoline derivative, was selected and analyzed. The stable structures of ClMQC molecule with minimum energy were investigated by density functional theory (DFT) together with B3LYP/6-311++G(d,p) method. It was seen that there are two different conformers (trans and cis) with minimum energy in the scanning made depending on the C─C─C=O dihedral angle. As a result of the calculation with the B3LYP/6-311++G(d,p) level, the energy difference (E+ZPV) between the two conformers was calculated as 14.60 kJ mol-1. Oscillator strength and excitation energies were analyzed by calculating the time-dependent DFT (TD-DFT). The energy differences between the excited energy levels are given in the graph. This was done by adding the ground state energies of both conformers. The energy corresponding to HOMO-LUMO was calculated to correspond to the S0→S2 transition for both conformers. The excitation energy values were calculated as 3.75 and 3.84 eV for trans and cis, respectively.

Anahtar Kelimeler

2-Chloro-7-Methylquinoline-3-Carbaldehyde, DFT/TD-DFT, Excitation energies, HOMO-LUMO

Destekleyen Kurum

Eskisehir Technical University Commission of Research Project

Proje Numarası

20ADP144

Teşekkür

This work was supported by the Eskisehir Technical University Commission of Research Project under grant no: 20ADP144.

Kaynakça

• [1] Runge FF. Ueber einige Produkte der Steinkohlendestillation. Ann Physik Und Chem, 1834; 31: 65-78.
• [2] Knorr L. Synthetische Versuche mit dem Acetessigester. Justus Liebigs Annalen der Chemie 1887: 238: 137-219.
• [3] Chevalier J, Bredin J, Mahamoud A, Malléa M, Barbe J, Pagès JM. Inhibitors of antibiotic efflux in resistant Enterobacter aerogenes and Klebsiella pneumoniae strains. Antimicrob Agents Chemother 2004; 48(3): 1043–1046.
• [4] Dassonneville L, Lansiaux A, Wattelet A, Wattez N, Mahieu C, Van Miert S, Pieters L, Bailly C. Cytotoxicity and cell cycle effects of the plant alkaloids cryptolepine and neocryptolepine: relation to drug-induced apoptosis. Eur J Pharmacol 2000; 409(1): 9-18.
• [5] Solomon VR, Lee H. Chloroquine and its analogs: A new promise of an old drug for effective and safe cancer therapies. Eur J Pharmacol 2009; 625: 220−33.
• [6] Vargas LY, Castelli MV, Kouznetsov VV, Urbina JM, Lopez SN, Sortino M, Enriz RD, Ribas JC, Zacchino S. In vitro Antifungal Activity of New Series of Homoallylamines and Related Compounds with Inhibitory Properties of the Synthesis of Fungal Cell Wall Polymers. Bioorg Med Chem 2003; 11: 1531−1550.
• [7] Ablordeppey SY, Fan P, Li S, Clark AM, Hufford CD. Substituted Indoloquinolines as New Antifungal Agents. Bioorg Med Chem 2002, 10, 1337−1346.
• [8] Wiesner J, Ortmann R, Jomaa H and Schlitzer M. New antimalarial drugs. Angew Chem Int Ed Engl 2003; 42: 5274−529.
• [9] Foley M, Tilley L. Quinoline antimalarials: mechanisms of action and resistance. Int J Parasitol 1997; 27(2): 231−40.
• [10] Vlok MC. Artemisinin-Quinoline Hybrids: Design, Synthesis and Antimalarial Activity. Ph.D. Thesis, North-West University, Potchefstroom, 2013.
• [11] Vandekerckhove S, D'hooghe M. Quinoline-based antimalarial hybrid compounds. Bioorg Med Chem 2015; 23: 5098–5119.
• [12] Augustijns P, Geusens P and Verbeke N. Chloroquine levels in blood during chronic treatment of patients with rheumatoid arthritis. Eur J Clin Pharmacol 1992; 42: 429−433.
• [13] Dondorp A, Nosten F, Stepniewska K, Day N, White N. South East Asian Quinine Artesunate Malaria Trial (SEAQUAMAT) group. Artesunate versus quinine for treatment of severe falciparum malaria: a randomized trial. Lancet 2005; 366: 717−25.
• [14] Paton JH, Reeves DS. Fluoroquinolone antibiotics. Microbiology, pharmacokinetics and clinical use. Drugs 1988; 36(2): 193−228.
• [15] Gordon GR and Walter A. Jacobs Synthesis of Substituted Quinolines and 5,6-Benzoquinolines. J Am Chem Soc 1939; 61: 2890–2895.
• [16] Madapa S, Tusi Z, Batra S. Advances in the Synthesis of Quinoline and Quinoline-Annulated Ring Systems. Curr Org Chem 2008; 12: 1116−1183.
• [17] Kuş N, Sagdinc S, Fausto R. Infrared Spectrum and UV-Induced Photochemistry of Matrix-Isolated 5-Hydroxyquinoline. J Phys Chem A 2015; 119(24):6296−308.
• [18] Kuş N, Henriques MS, Paixão JS, Lapinski L and Fausto R. Crystal Structure, Matrix-Isolation FTIR, and UV-Induced Conformational Isomerization of 3-Quinolinecarboxaldehyde. J Phys Chem A 2014; 118 (38): 8708−8716.
• [19] Horta PC, Henriques MSC, Kuş N, Paixão JA, O'Neill PM, Cristiano MLS, Fausto R. Synthesis, structural and conformational analysis, and IR spectra of ethyl 4-chloro-7-iodoquinoline-3-carboxylate Tetrahedron 2015; 71: 7583−7592.
• [20] Horta P, Kuş N, Henriques MS, Paixão JA, Coelho L, Nogueira F, O'Neill PM, Fausto R, Cristiano ML. Quinolone-Hydroxyquinoline Tautomerism in Quinolone 3-Esters. Preserving the 4-Oxoquinoline Structure To Retain Antimalarial Activity. J Org Chem 2015; 80(24): 12244−57.
• [21] Frisch MJ et al. Gaussian 09, Revision A.0.2. Gaussian Inc, Wallingford CT, 2009. [22] Becke AD. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A 1988; 38: 3098–3100.
• [23] Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 1988; 37: 785–789.
• [24] Reed AE, Curtiss LA, Weinhold F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev 1988; 88: 899–926.
• [25] Weinhold F, Landis CR. Valency and Bonding. A Natural Bond Orbital Donor-Acceptor Perspective. Cambridge University Press: New York, 2005.
• [26] Bauernschmitt R, Ahlrichs R. Treatment of Electronic Excitations Within the Adiabatic Approximation of Time Dependent Density Functional Theory. Chem Phys Lett 1996; 256: 454−464.
• [27] Stratmann RE, Scuseria GE, Frisch MJ. An Efficient Implementation of Time-Dependent Density-Functional Theory for the Calculation of Excitation Energies of Large Molecules. J Chem Phys 1998; 109: 8218−8224.
• [28] Avadanei M, Kuş N, Cozan V and Fausto R. Structure and Photochemistry of N‑Salicylidene‑p‑carboxyaniline Isolated in Solid Argon. J Phys Chem A 2015; 119: 9121−9132.