An improved synthesis, spectroscopic (FT-IR, NMR) study and DFT computational analysis (IR, NMR, UV-Vis, MEP diagrams, NBO, NLO, FMO) of the 1,5-methanoazocino[4,3-b]indole core structure

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dc.authorid0000-0002-2819-3612
dc.authorscopusid6507868758
dc.authorscopusid36447801100
dc.authorwosiduludag, Nesimi/AAB-1353-2020
dc.authorwosidSerdaroğlu, Goncagül/I-6780-2016
dc.contributor.authorUludağ, Nesimi
dc.contributor.authorSerdaroğlu, Goncagül
dc.date.accessioned2022-05-11T14:30:58Z
dc.date.available2022-05-11T14:30:58Z
dc.date.issued2018
dc.departmentFakülteler, Fen Edebiyat Fakültesi, Kimya Bölümü
dc.description.abstractThis study examines the synthesis of azocino[4,3-b]indole structure, which constitutes the tetracyclic framework of uleine, dasycarpidoneand tubifolidineas well as ABDE substructure of the strychnosalkaloid family. It has been synthesized by Fischer indolization of 2 and through the cylization of 4 by 2,3-dichlor-5-6-dicyanobenzoquinone (DDQ). H-1 and C-1 NMR chemical shifts have been predicted with GIAO approach and the calculated chemical shifts show very good agreement with observed shifts. FT-IR spectroscopy is important for the analysis of functional groups of synthesized compounds and we also supported FT-IR vibrational analysis with computational IR analysis. The vibrational spectral analysis was performed at B3LYP level of the theory in both the gas and the water phases and it was compared with the observed IR values for the important functional groups. The DFF calculations have been conducted to determine the most stable structure of the 1,2,3,4,5,6,7-Hexahydro-1,5-methanoazocino [4,3-b] indole (5). The Frontier Molecular Orbital Analysis, quantum chemical parameters, physicochemical properties have been predicted by using the same theory of level in both gas phase and the water phase, at 631 + g** and 6311++g** basis sets. TD- DFF calculations have been performed to predict the UV- Vis spectral analysis for this synthesized molecule. The Natural Bond Orbital (NBO) analysis have been performed at B3LYP level of theory to elucidate the intra-molecular interactions such as electron delocalization and conjugative interactions. NLO calculations were conducted to obtain the electric dipole moment and polarizability of the title compound. (C) 2017 Elsevier B.V. All rights reserved.
dc.description.sponsorshipScientific and technical research Council (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [112T503]; scientific research projects of Cumhuriyet UniversityCumhuriyet University [EGT-066]
dc.description.sponsorshipSupport of this work by the Scientific and technical research Council (TUBITAK) through Project 112T503 is gratefully acknowledged. Also, thanks to acknowledge the financial support of the scientific research projects of Cumhuriyet University (Project No: EGT-066). The all calculations have been conducted at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure).
dc.identifier.doi10.1016/j.molstruc.2017.11.032
dc.identifier.endpage560
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85034422376
dc.identifier.scopusqualityQ2
dc.identifier.startpage548
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2017.11.032
dc.identifier.urihttps://hdl.handle.net/20.500.11776/7259
dc.identifier.volume1155
dc.identifier.wosWOS:000424717800059
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorUludağ, Nesimi
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subject1,5-methanoazocino[4,3-b]indole synthesize
dc.subjectNBO
dc.subjectNLO
dc.subjectFMO
dc.subjectNMR
dc.subjectFT-IR
dc.subjectAb-Initio Hf
dc.subject1st-Order Hyperpolarizability
dc.subjectHomo-Lumo
dc.subjectMolecular-Structure
dc.subjectIndole Alkaloids
dc.subjectFacile Synthesis
dc.subjectRaman
dc.subjectRoute
dc.subjectFramework
dc.subjectSpectra
dc.titleAn improved synthesis, spectroscopic (FT-IR, NMR) study and DFT computational analysis (IR, NMR, UV-Vis, MEP diagrams, NBO, NLO, FMO) of the 1,5-methanoazocino[4,3-b]indole core structure
dc.typeArticle

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