Research Journal of Pharmacy and Technology

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Computational Study on Molecular Structure, Uv-visible and Vibrational Spectra and Frontier Molecular Orbital Analysis Of (E)-7-((2-chloroquinolin-3-yl)Methylene)-1,2,6,7-tetrahydro-8h-indeno[5,4-b]Furan-8-one


Affiliations
1 Department of Chemistry, Mahatma Gandhi Vidyamandir’s Arts, Science and Commerce College, Manmad, Nashik - 423104, (Affiliated to SP Pune University, Pune), India
2 Department of Chemistry, Mahant Jamanadas Maharaj Arts, Commerce and Science College, Karanjali, Taluka - Peth, District – Nashik - 422 208,, India
3 Department of Chemistry, Mahatma Gandhi Vidyamandir’s Arts, Science and Commerce College, Manmad, Nashik - 423104, India (Affiliated to SP Pune University, Pune), India
     

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Quinoline scaffold is one of the most often perceived parts in biologically active organic compounds. In light of this, an quinoline containing 2-arylidene derivative; (E)-7-((2-chloroquinolin-3-yl)methylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (2-CQMIF) is studied by using density functional theory (DFT) at B3LYP/6-311G(d,p) basis set. The geometry of the 2-CQMIF molecule was optimized by using B3LYP/6-311G(d,p) basis set and in-depth structural analysis on bond lengths and bond angles has been discussed. The frontier molecular orbital (FMO) analysis and various quantum chemical parameters are calculated and discussed for the better understanding of chemical behavior of the title molecule. The theoretical and experimental UV-Visible absorption bands are compared. The TD-DFT method at B3LYP/6-311G(d,p) basis set was employed to predict the electronic excitations. The scaled theoretical vibrational assignments calculated at 6-311G(d,p) level are compared with the experimental results and the good agreement is observed between them. Molecular electrostatic potential (MEP) surface investigation is presented to understand the reactivity sites of the title molecule. Besides, some thermodynamic properties have also been computed at same level of theory.

Keywords

B3LYP/6-311G(d,p), Quinoline, Time Dependent DFT, HOMO-LUMO.
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  • Chibale K, Moss JR, Blackie M, van Schalkwyk D, Smith PJ. New amine and urea analogs of ferrochloroquine: Synthesis, antimalarial activity in vitro and electrochemical studies. Tetrahedron Letters. 2000; 41(32): 6231-6235.

  • Singh B, Chetia D, Puri SK, Srivastava K, Prakash A, Synthesis and in vitro and in vivo antimalarial activity of novel 4-anilinoquinoline Mannich base derivatives. Medicinal Chemistry Research. 2011; 20(9): 1523-1529.

  • Bhat HR, Singh UP, Gahtori P, Ghosh SK, Gogoi K, Prakash A, Singh RK. Antimalarial activity and docking studies of novel bi-functional hybrids derived from 4-aminoquinoline and 1,3,5-triazine against wild and mutant malaria parasites as pf-DHFR inhibitor. RSC Advances. 2013; 3(9): 2942-2952.

  • Gilbert AM, Bursavich MG, Lombardi S, Georgiadis KE, Reifenberg E, Flannery CR, Morris EA. N-((8-Hydroxy-5-substituted-quinolin-7-yl)(phenyl) methyl)-2-phenyloxy/amino-acetamide inhibitors of ADAMTS-5 (Aggrecanase-2). Bioorganic & Medicinal Chemistry Letters. 2008; 18(24): 6454-6457.

  • Elsayed Khidre R, Fathy Abdel-Wahab B, Abdel-Rehem Badria F. New quinoline-based compounds for analgesic and anti-inflammatory evaluation. Letters in Drug Design & Discovery. 2011; 8(7):640-648.

  • Fu HG, Li ZW, Hu XX, Si SY, You XF, Tang S, Wang YX, Song DQ. Synthesis and biological evaluation of quinoline derivatives as a novel class of broad-spectrum antibacterial agents. Molecules. 2019; 24(3): 548.

  • Musiol R, Jampilek J, Buchta V, Silva L, Niedbala H, Podeszwa B, Palka A, Majerz-Maniecka K, Oleksyn B, Polanski J. Antifungal properties of new series of quinoline derivatives. Bioorganic & Medicinal Chemistry. 2006; 14(10): 3592-3598.

  • Nasr EE, Mostafa AS, El‐Sayed MA, Massoud MA. Design, synthesis, and docking study of new quinoline derivatives as antitumor agents. Archiv der Pharmazie. 2019; 352(7): 1800355.

  • Marganakop SB, Kamble RR, Hoskeri J, Prasad DJ, Meti GY. Facile synthesis of novel quinoline derivatives as anticancer agents. Medicinal Chemistry Research. 2014; 23(6): 2727-2735.

  • De la Guardia C, Stephens DE, Dang HT, Quijada M, Larionov OV, Lleonart R. Antiviral activity of novel quinoline derivatives against dengue virus serotype 2. Molecules. 2018; 23(3): 672.

  • Rossiter S, Peron JM, Whitfield PJ, Jones K. Synthesis and anthelmintic properties of arylquinolines with activity against drug-resistant nematodes. Bioorganic & Medicinal Chemistry Letters. 2005; 15(21): 4806-4818.

  • Hochegger P, Faist J, Seebacher W, Saf R, Mäser P, Kaiser M, Weis R. Antiprotozoal Activities of Tetrazole-quinolines with Aminopiperidine Linker. Medicinal Chemistry. 2019; 15(4): 409-416.

  • Marella A, Tanwar OP, Saha R, Ali MR, Srivastava S, Akhter M, Shaquiquzzaman M, Alam MM. Quinoline: A versatile heterocyclic. Saudi Pharmaceutical Journal. 2013; 21(1): 1-2.

  • Hussaini SM. Therapeutic significance of quinolines: a patent review (2013-2015). Expert Opinion on Therapeutic Patents. 2016; 26(10): 1201-1221.

  • Bi Y, Stoy P, Adam L, He B, Krupinski J, Normandin D, Pongrac R, Seliger L, Watson A, Macor JE. Quinolines as extremely potent and selective PDE5 inhibitors as potential agents for treatment of erectile dysfunction. Bioorganic & Medicinal Chemistry Letters. 2004; 14(6): 1577-1580.

  • Wang XQ, Zhao CP, Zhong LC, Zhu DL, Mai DH, Liang MG, He MH. Preparation of 4-Flexible Amino-2-Arylethenyl-Quinoline Derivatives as Multi-target Agents for the Treatment of Alzheimer’s Disease. Molecules. 2018; 23(12): 3100.

  • Bawa S, Kumar S, Drabu S, Kumar R. Structural modifications of quinoline-based antimalarial agents: recent developments. Journal of Pharmacy and Bioallied Sciences. 2010; 2(2): 64-71.

  • Huang L, Lu C, Sun Y, Mao F, Luo Z, Su T, Jiang H, Shan W, Li X. Multitarget-directed benzylideneindanone derivatives: anti-β-amyloid (Aβ) aggregation, antioxidant, metal chelation, and monoamine oxidase B (MAO-B) inhibition properties against Alzheimer’s disease. Journal of Medicinal Chemistry. 2012; 55(19): 8483-8492.

  • Patil V, Barragan E, Patil SA, Patil SA, Bugarin A. Direct synthesis and antimicrobial evaluation of structurally complex chalcones. Chemistry Select, 2016: 1(13): 3647-3650.

  • Katila P, Shrestha A, Shrestha A, Shrestha R, Park PH, Lee ES. Design and Synthesis of Fluorinated and/or Hydroxylated 2‐Arylidene‐1‐indanone Derivatives as an Inhibitor of LPS‐stimulated ROS Production in RAW 264.7 Macrophages with Structure–Activity Relationship Study. Bulletin of the Korean Chemical Society. 2018; 39(12): 1432-1441.

  • Adole VA, Jagdale BS, Pawar TB, Sagane AA. Ultrasound promoted stereoselective synthesis of 2,3-dihydrobenzofuran appended chalcones at ambient temperature. South African Journal of Chemistry. 2020; 73: 35-43.

  • Gomes MN, Braga RC, Grzelak EM, Neves BJ, Muratov E, Ma R, Klein LL, Cho S, Oliveira GR, Franzblau SG, Andrade CH. QSAR-driven design, synthesis and discovery of potent chalcone derivatives with antitubercular activity. European Journal of Medicinal Chemistry. 2017; 137: 126-138.

  • Avila-Villarreal G, Hernández-Abreu O, Hidalgo-Figueroa S, Navarrete-Vázquez G, Escalante-Erosa F, Peña-Rodríguez LM, Villalobos-Molina R, Estrada-Soto S. Antihypertensive and vasorelaxant effects of dihydrospinochalcone-A isolated from Lonchocarpus xuul Lundell by NO production: Computational and ex vivo approaches. Phytomedicine. 2013; 20(14): 1241-1246.

  • Faidallah HM, Rostom SA, Khan KA. Synthesis and biological evaluation of pyrazole chalcones and derived bipyrazoles as anti-inflammatory and antioxidant agents. Archives of Pharmacal Research. 2015; 38(2): 203-215.

  • Kamal A, Balakrishna M, Loka Reddy V, Riyaz S, Bagul C, Satyanarayana BM, Venkateswar Rao J. Synthesis and Biological Evaluation of Benzo [d][1,3] Dioxol‐5‐yl Chalcones as Antiproliferating Agents. Chemical Biology & Drug Design. 2015; 86(5): 1267-1284.

  • Wan Z, Hu D, Li P, Xie D, Gan X. Synthesis, antiviral bioactivity of novel 4-thioquinazoline derivatives containing chalcone moiety. Molecules. 2015; 20(7): 11861-11874.

  • Moodley T, Momin M, Mocktar C, Kannigadu C, Koorbanally NA. The synthesis, structural elucidation and antimicrobial activity of 2‐and 4‐substituted‐coumarinyl chalcones. Magnetic Resonance in Chemistry. 2016; 54(7): 610-617.

  • Chaudhari MB, Moorthy S, Patil S, Bisht GS, Mohamed H, Basu S, Gnanaprakasam B. Iron-catalyzed batch/continuous flow C–H functionalization module for the synthesis of anticancer peroxides. The Journal of Organic Chemistry. 2018; 83(3): 1358-1368.

  • Chaudhari MB, Jayan K, Gnanaprakasam B. Sn-Catalyzed Criegee-Type Rearrangement of Peroxyoxindoles Enabled by Catalytic Dual Activation of Esters and Peroxides. The Journal of Organic Chemistry. 2020; 85(5): 3374-3382.

  • Chaudhari MB, Bisht GS, Kumari P, Gnanaprakasam B. Ruthenium-catalyzed direct α-alkylation of amides using alcohols. Organic & Biomolecular Chemistry. 2016; 14(39): 9215-9220.

  • Chaudhari MB, Mohanta N, Pandey, AM, Vandana M, Karmodiya K, Gnanaprakasam B. Peroxidation of 2-oxindole and barbituric acid derivatives under batch and continuous flow using an eco-friendly ethyl acetate solvent. Reaction Chemistry & Engineering. . 2019; 4(7): 1277-1283.

  • Adole VA, Pawar TB, Jagdale BS. Aqua‐mediated rapid and benign synthesis of 1,2,6,7‐tetrahydro‐8H‐indeno[5,4‐b] furan‐8‐one‐appended novel 2‐arylidene indanones of pharmacological interest at ambient temperature. Journal of the Chinese Chemical Society. 2020; 67(2): 306-315.

  • Adole VA. Synthetic approaches for the synthesis of dihydropyrimidinones/thiones (biginelli adducts): a concise review. World Journal of Pharmaceutical Research. 2020; 9(6): 1067-1091.

  • Adole VA, Pawar TB, Koli PB, Jagdale BS. Exploration of catalytic performance of nano-La2O3 as an efficient catalyst for dihydropyrimidinone/thione synthesis and gas sensing. Journal of Nanostructure in Chemistry. 2019; 9(1): 61-76.

  • Patil BN, Lade JJ, Parab AA, Sathe PA, Vadagaonkar KS, Chaskar AC. NBS-assisted an efficient conversion of styrenes to α-hydroxy ketones in water. Tetrahedron Letters. 2019; 60(27):1788-1791.

  • Lade JJ, Patil BN, Sathe PA, Vadagaonkar KS, Chetti P, Chaskar AC. Iron Catalyzed Cascade Protocol for the Synthesis of Pyrrolo [1, 2‐a] quinoxalines: A Powerful Tool to Access Solid State Emissive Organic Luminophores. Chemistry Select. 2017; 2(23): 6811-6817.

  • Patil BN, Lade JJ, Pardeshi SD, Patil P, Chaskar AC. Polyethylene‐Glycol‐(PEG‐400) Mediated Environmentally Benign Protocol for the Synthesis of Pyrrolo [1,2‐a] quinoxalines from Benzyl Amines at Room Temperature. Chemistry Select. 2019; 4(38): 11362-11366.

  • Adole VA, More RA, Jagdale BS, Pawar TB, Chobe SS. Efficient synthesis, antibacterial, antifungal, antioxidant and cytotoxicity study of 2‐(2‐hydrazineyl) thiazole derivatives. Chemistry Select. 2020; 5(9): 2778-2786.

  • Chobe SS, Adole VA, Deshmukh KP, Pawar TB, Jagdale BS. Poly (ethylene glycol)(PEG-400): A green approach towards synthesis of novel pyrazolo [3, 4-d] pyrimidin-6-amines derivatives and their antimicrobial screening. Archives of Applied Science Research. 2014; 6(2): 61-66.

  • Parlak C, Ramasami P, Tursun M, Rhyman L, Kaya MF, Atar N, Alver Ö, Şenyel M. 4-Mercaptophenylboronic acid: Conformation, FT-IR, Raman, OH stretching and theoretical studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2015; 144: 131-138.

  • Govindarasu K, Kavitha E. Molecular structure, vibrational spectra, NBO, UV and first order hyperpolarizability, analysis of 4-Chloro-dl-phenylalanine by density functional theory. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2014; 133: 799-810.

  • Rani U, Karabacak M, Tanrıverdi O, Kurt M, Sundaraganesan N. The spectroscopic (FTIR, FT-Raman, NMR and UV), first-order hyperpolarizability and HOMO–LUMO analysis of methylboronic acid. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2012; 92: 67-77.

  • Adole VA, Waghchaure RH, Jagdale BS, Pawar TB, Pathade SS. Molecular structure, frontier molecular orbital and spectroscopic examination on dihydropyrimidinones: a comparative computational approach. Journal of Advanced Scientific Research, 2020; 11(2): 64-70.

  • Sebastian S, Sylvestre S, Sundaraganesan N, Amalanathan M, Ayyapan S, Oudayakumar K, Karthikeyan B. Vibrational spectra, molecular structure, natural bond orbital, first order hyperpolarizability, TD-DFT and thermodynamic analysis of 4-amino-3-hydroxy-1-naphthalenesulfonic acid by DFT approach. Spectrochimica Acta Part A. Molecular and Biomolecular Spectroscopy. 2013; 107: 167-178.

  • Sawant AB, Nirwan RS. Synthesis, characterization and DFT studies of 6, 8-dichloro-2-(4-chlorophenyl)-4H-chromen-4-one. Indian Journal of Pure & Applied Physics. 2012; 50(1): 308-313,

  • Sawant AB, Gill CH, Nirwan RS. Molecular structure and vibrational spectra of 2-[5-(4-chlorophenyl)-4, 5-dihydro-1H-pyrazol-3-yl] phenol. Indian Journal of Pure & Applied Physics. 2012; 50(1): 38-44.

  • Adole VA, Waghchaure RH, Jagdale BS, Pawar TB. Investigation of Structural and Spectroscopic Parameters of Ethyl 4-(4-isopropylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate: a DFT Study. Chemistry & Biology Interface. 2020; 10(1): 22-30.

  • Adole VA, Waghchaure RH, Pathade SS, Patil MR, Pawar TB, Jagdale BS. Solvent-free grindstone synthesis of four new (E)-7-(arylidene)-indanones and their structural, spectroscopic and quantum chemical study: a comprehensive theoretical and experimental exploration. Molecular Simulation. 2020; 46(14): 1045-1054.

  • Adole VA, Pawar TB, Jagdale BS. DFT computational insights into structural, electronic and spectroscopic parameters of 2-(2-Hydrazineyl) thiazole derivatives: a concise theoretical and experimental approach. Journal of Sulfur Chemistry. 2020:1-8.

  • Mohammed HK, Ayyash AN. Vibrational Spectroscopy, Molecular properties, IR, UV-Visible, NMR Spectra and (HF, DFT) Calculations of Organic Molecule. Asian Journal of Research in Chemistry. 2019;12(5):274-277.

  • Ghammamy S, Qaitmas NA, Lashgari A. Structural Properties, Natural Bond Orbital, Theory Functional Calculations (DFT), and Energies for the Two New Halo Organic Compounds. Asian Journal of Research in Chemistry. 2015;8(1):60-65.

  • Dhonnar SL, Adole VA, Sadgir NV, Jagdale BS. Structural, Spectroscopic (UV-Vis and IR), Electronic and Chemical Reactivity Studies of (3,5-Diphenyl-4, 5-dihydro-1H-pyrazol-1-yl)(phenyl) methanone. Physical Chemistry Research. 2021; 9(2): 193-209.

  • Lashgari A, Ghammamy S, Shahsavari M. Theoretical and Density Functional Theory (DFT) studies for the organic compound: 2-Amino-6-chloro-N-methylbenzamide. Asian Journal of Research in Chemistry. 2014 Jul 28;7(7):677-680.

  • Pawar TB, Jagdale BS, Sawant AB, Adole VA. DFT Studies of 2-[(2-substitutedphenyl) carbamoyl] benzoic acids. Journal of Chemical, Biological and Physical Sciences. 2017;7:167-175.

  • Hassan MF, Ayyash AN. Study of Spectral and Molecular Properties of Polyatomic molecule by Semiempirical and DFT Methods. Asian Journal of Research in Chemistry. 2019; 12(6): 330-334.

  • Adole VA, Koli PB, Shinde RA, Shinde RS. Computational Insights on Molecular Structure, Electronic Properties, and Chemical Reactivity of (E)-3-(4-Chlorophenyl)-1-(2-Hydroxyphenyl) Prop-2-en-1-one. Material Science Research India. 2020;17(special issue 2020):41-53.

  • Jayanna ND. An efficient synthesis of 2-(6-methoxy-2-napthyl)-1, 3-benzoxazole derivatives using IBD/LTA: Reactivity, DFT, Anticancer and Larvicidal activities. Asian Journal of Research in Chemistry. 2020;13(5):312-318.

  • Adole VA, Jagdale BS, Pawar TB, Desale BS. Molecular structure, frontier molecular orbitals, MESP and UV–visible spectroscopy studies of Ethyl 4-(3, 4-dimethoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate: A theoretical and experimental appraisal. Material Science Research India. 2020;17(special issue2020):13-36.

  • Pathade SS, Adole VA, Jagdale BS, Pawar TB. Molecular structure, electronic, chemical and spectroscopic (UV-visible and IR) studies of 5-(4-chlorophenyl)-3-(3, 4-dimethoxyphenyl)-1-phenyl-4, 5-dihydro-1H-pyrazole: combined DFT and experimental exploration. Material Science Research India. 2020; 17(special issue 2020):27-40.

  • Siahgali S, Ghammamy S. Theoretical Functional Calculations (DFT) Studies of Structural Properties of 1-Benzoyl-3-[(2-benzyl Sulfanyl) phenyl] thiourea with Comparison of Experimental Data. Asian Journal of Research in Chemistry. 2014;7(1):62-66.

  • Kumari BJ, Reji TA. Spectroscopic Investigation, HOMO-LUMO and Mulliken analysis of 2-[2-(Butylamino-4-phenylaminothiazol)-5-oyl] benzothiazole by DFT study. Asian Journal of Research in Chemistry. 2017;10(6):819-826.

  • Shinde RA, Adole VA, Jagdale BS, Pawar TB, Desale BS, Shinde RS. Efficient Synthesis, Spectroscopic and Quantum Chemical Study of 2,3-Dihydrobenzofuran Labelled Two Novel Arylidene Indanones: A Comparative Theoretical Exploration. Material Science Research India. 2020;17(2):146-61.

  • Sangeetha S, Reji TF. Molecular Geometry, Vibrational Assignments, HOMO-LUMO, Mulliken's charge analysis and DFT Calculations of 2-(2-Phenylaminothiazole-5-oyl) 1-methyl-6-methylbenzimidazole. Asian Journal of Research in Chemistry. 2018; 11(6): 848-856.

  • Pokharia S. A Density Functional Theory (DFT) study on di-n-butyltin (IV) derivative of glycyltryptophane. Asian Journal of Research in Chemistry. 2016; 9(2):53-61.

  • Shinde RA, Adole VA, Jagdale BS, Pawar TB. Experimental and Theoretical Studies on the Molecular Structure, FT-IR, NMR, HOMO, LUMO, MESP, and Reactivity Descriptors of (E)-1-(2,3-Dihydrobenzo [b][1,4] dioxin-6-yl)-3-(3,4,5-trimethoxyphenyl) prop-2-en-1-one. Material Science Research India. 2020; 17(special issue 2020): 54-72.

  • Pokharia S. Theoretical insights on Organotin (IV)-protein interaction: Density Functional Theory (DFT) studies on di-n-butyltin (IV) derivative of Glycylvaline. Asian Journal of Research in Chemistry. 2015; 8(1):7-12.

  • Sawant AB, Nirwan RS. Synthesis, characterization and DFT studies of 6,8-dichloro-2-(4-chlorophenyl)-4H-chromen-4-one. Indian Journal of Pure and Applied Physics. 2012;50:308-313.

  • Nirwan RS, Sawant AB. Experimental and theoretical studies of 6,8-dichloro-2-(4-methoxyphenyl)-4H-chromen-4-one. Rasāyan Journal of Chemistry. 2011;4:613-619.

  • Sadgir NV, Dhonnar SL, Jagdale BS, Sawant AB. Synthesis, spectroscopic characterization, XRD crystal structure, DFT and antimicrobial study of (2E)-3-(2,6-dichlorophenyl)-1-(4-methoxyphenyl)-prop-2-en-1-one. SN Applied Sciences. 2020; 2(8): 1-12.

  • Sadgir NV, Dhonnar SL, Jagdale BS, Waghmare B, Sadgir C, Synthesis, Spectroscopic Characterization, Quantum Chemical Study and Antimicrobial Study of (2e)-3-(2, 6-Dichlorophenyl)-1-(4-Fluoro)-Prop-2-En-1-One. Material Science Research India. 2020; 17(3): 281-293.

  • Dhonnar SL, Jagdale BS, Sawant AB, Pawar TB, Chobe SS, Molecular structure, vibrational spectra and theortical HOMO–LUMO analysis of (E)-3,5-dimethyl-1-phenyl-4-(p-tolyldiazenyl)-1H-pyrazole by DFT method. Der Pharma Chemica. 2016; 8(17): 119-128.

  • Adole VA, Computational Chemistry Approach for the Investigation of Structural, Electronic, Chemical and Quantum Chemical Facets of Twelve Biginelli Adducts. Journal of Applied Organometallic Chemistry. 2021;1(1):29-40.

  • Adole VA, Bagul VR, Ahire SA, Pawar RK, Yelmame GB, Bukane AR, Computational chemistry: molecular structure, spectroscopic (UV-visible and IR), electronic, chemical and thermochemical analysis of 3'-phenyl-1,2- dihydrospiro[indeno[5,4-b]. Journal of Advanced Scientific Research. 2021; 12(1) Suppl 1:276-286.

  • Halim SA, Ibrahim MA. Synthesis, DFT computational insights on structural, optical, photoelectrical characterizations and spectroscopic parameters of the novel (2E)-3-(4-methoxy-5-oxo-5H-furo [3,2-g] chromen-6-yl) acrylonitrile (MOFCA). Journal of Molecular Structure. 2021;1223:129316.

  • Halim SA, Ibrahim MA. Synthesis, DFT calculations, electronic structure, electronic absorption spectra, natural bond orbital (NBO) and nonlinear optical (NLO) analysis of the novel 5-methyl-8H-benzo [h] chromeno [2,3-b][1, 6] naphthyridine-6 (5H), 8-dione (MBCND). Journal of Molecular Structure. 2017; 1130: 543-558.

  • Farag AAM, Roushdy N, Halim SA, El-Gohary NM, Ibrahim MA, Said S. Synthesis, molecular, electronic structure, linear and non-linear optical and phototransient properties of 8-methyl-1,2-dihydro-4H-chromeno [2,3-b] quinoline-4,6 (3H)-dione (MDCQD): Experimental and DFT investigations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2018; 191: 478-490.

  • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery Jr JA, Vreven T, Kudin KN, Burant JC, Millam JM. Gaussian 03, Revision C. 02. Wallingford, CT: Gaussian. Inc. 2004.

  • Szafran M, Katrusiak A, Koput J, Dega-Szafran Z. X-ray, MP2 and DFT studies of the structure, vibrational and NMR spectra of homarine. Journal of Molecular Structure. 2007; 846(1-3):1-12.

  • Dereli Ö, Sudha S, Sundaraganesan N. Molecular structure and vibrational spectra of 4-phenylsemicarbazide by density functional method. Journal of Molecular Structure. 2011; 994(1-3): 379-386.


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  • Computational Study on Molecular Structure, Uv-visible and Vibrational Spectra and Frontier Molecular Orbital Analysis Of (E)-7-((2-chloroquinolin-3-yl)Methylene)-1,2,6,7-tetrahydro-8h-indeno[5,4-b]Furan-8-one

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Authors

Vishnu A. Adole
Department of Chemistry, Mahatma Gandhi Vidyamandir’s Arts, Science and Commerce College, Manmad, Nashik - 423104, (Affiliated to SP Pune University, Pune), India
Abhijit R. Bukane
Department of Chemistry, Mahatma Gandhi Vidyamandir’s Arts, Science and Commerce College, Manmad, Nashik - 423104, (Affiliated to SP Pune University, Pune), India
Ravindra H. Waghchaure
Department of Chemistry, Mahant Jamanadas Maharaj Arts, Commerce and Science College, Karanjali, Taluka - Peth, District – Nashik - 422 208,, India
Rohit S. Shinde,
Department of Chemistry, Mahant Jamanadas Maharaj Arts, Commerce and Science College, Karanjali, Taluka - Peth, District – Nashik - 422 208,, India
Bapu S. Jagdale
Department of Chemistry, Mahatma Gandhi Vidyamandir’s Arts, Science and Commerce College, Manmad, Nashik - 423104, India (Affiliated to SP Pune University, Pune), India

Abstract


Quinoline scaffold is one of the most often perceived parts in biologically active organic compounds. In light of this, an quinoline containing 2-arylidene derivative; (E)-7-((2-chloroquinolin-3-yl)methylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (2-CQMIF) is studied by using density functional theory (DFT) at B3LYP/6-311G(d,p) basis set. The geometry of the 2-CQMIF molecule was optimized by using B3LYP/6-311G(d,p) basis set and in-depth structural analysis on bond lengths and bond angles has been discussed. The frontier molecular orbital (FMO) analysis and various quantum chemical parameters are calculated and discussed for the better understanding of chemical behavior of the title molecule. The theoretical and experimental UV-Visible absorption bands are compared. The TD-DFT method at B3LYP/6-311G(d,p) basis set was employed to predict the electronic excitations. The scaled theoretical vibrational assignments calculated at 6-311G(d,p) level are compared with the experimental results and the good agreement is observed between them. Molecular electrostatic potential (MEP) surface investigation is presented to understand the reactivity sites of the title molecule. Besides, some thermodynamic properties have also been computed at same level of theory.

Keywords


B3LYP/6-311G(d,p), Quinoline, Time Dependent DFT, HOMO-LUMO.

References