An efficient studies on C-2 cyanomethylation of the indole synthesis: the electronic and spectroscopic characterization (FT-IR, NMR, UV-Vis), antioxidant activity, and theoretical calculations

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dc.authorscopusid6507868758
dc.authorscopusid36447801100
dc.contributor.authorUludağ, Nesimi
dc.contributor.authorSerdaroğlu, Goncagül
dc.date.accessioned2022-05-11T14:31:06Z
dc.date.available2022-05-11T14:31:06Z
dc.date.issued2022
dc.departmentFakülteler, Fen Edebiyat Fakültesi, Kimya Bölümü
dc.description.abstractThe direct cynamethylation with the development of catalyzed methodologies directed to 2-(cyanomethyl)indoles was reported by using tetrafluoro-1,4-benzoquinone (TFB) as the catalyst and it was synthesized in one step without protecting the indole N-H. Due to the plenty of synthesis indole moieties is currently the object of extensive investigations due to their biologically interesting role as the recognized block in many natural products and bioactive products. Moreover, the desired products were achieved in good yields. The antioxidant activity of the intermediates and the final product was explored by the DPPH method, and the results disclosed that the intermediate R2a and the final product could be used as promising agents in biomedicinal research. The structural and physicochemical properties of the intermediate and product indoles were enlightened by DFT calculations at B3LYP/6-311G(d,p) level, in the gas, CHCl3, methanol, and water environments. The TD-DFT calculations at the same level of theory were performed to compare with the recorded spectra of the studied compounds and to illuminate the possible electronic transitions (s(0) > s(n)) underlying the observed peaks. The NBO analyses of the compounds indicated that the n -> pi* and pi -> pi* interactions were a great portion of the lowering of the stabilization energy. The FMO analyses displayed that the intermediates and product, but the intermediate R2a mostly in all solvents, tended the electrodonating capability to the external molecular system. (C) 2021 Elsevier B.V. All rights reserved.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [112T503]; Sivas Cumhuriyet University scientific research projects department [CUBAP: E. GT-090]
dc.description.sponsorshipWe are grateful to the Scientific and Technological Research Council of Turkey (TUBITAK Project No.112T503) for financial support and by the Sivas Cumhuriyet University scientific research projects department (Project No: CUBAP: E. GT-090). All calculations have been carried out at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure).
dc.identifier.doi10.1016/j.molstruc.2021.131416
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85114694919
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2021.131416
dc.identifier.urihttps://hdl.handle.net/20.500.11776/7318
dc.identifier.volume1247
dc.identifier.wosWOS:000709611000003
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.subjectIndole
dc.subjectReaction mechanism
dc.subjectAntioxidant activity
dc.subjectDFT and TD-DFT calculations
dc.subjectQuantum-Chemical Descriptors
dc.subjectDensity-Functional Theory
dc.subjectExcitation-Energies
dc.subjectBasis-Set
dc.subjectDft
dc.subjectNbo
dc.subjectFmo
dc.subjectMep
dc.subjectNlo
dc.subjectAldoximes
dc.titleAn efficient studies on C-2 cyanomethylation of the indole synthesis: the electronic and spectroscopic characterization (FT-IR, NMR, UV-Vis), antioxidant activity, and theoretical calculations
dc.typeArticle

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