Cyanomethylation of 2,3,4,9-tetrahydro-1H-carbazol-1-one based on using two different reagents: Antioxidant activity and DFT studies

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dc.authorscopusid36447801100
dc.authorscopusid6507868758
dc.authorscopusid6508161441
dc.contributor.authorSerdaroğlu, Goncagül
dc.contributor.authorUludağ, Nesimi
dc.contributor.authorErçağ, Erol
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.abstractC-2 and C-6 monoalkyl nitrile substituted reactant (1), which constitute the tricyclic framework of carbazole derivatives along with the substructure of the Strychnos alkaloids family, have been synthesized by using different bases to produce substitution reactions. In addition, the antioxidant capacity of the synthesized compound by the CUPRAC (cupric reducing antioxidant capacity) method was evaluated and the obtained TEAC (Trolox equivalent antioxidant capacity) coefficient implied that product (2) has antioxidant feature. The B3LYP/6-311G(d,p) level calculations were performed in the gas phase, and the optimized geometries obtained from these calculations were used for the solvation media calculations. The SMD variation of the IEFPCM (polarized continuum model) was used to conduct the quantum chemical calculations in the solvent environment such as CHCl3, CH3OH, and H2O (water, epsilon=78.4). Also, the NMR chemical shifts of the products were calculated using GIAO (Gauge-Independent Atomic Orbital) approach and compared with the corresponding experimental data. The TD-DFT calculations disclosed that the observed peaks for both products were attributed to the n -> pi* and pi -> pi* excitations. Moreover, NBO analysis revealed that the n -> pi* and pi -> pi* interactions have a great importance for lowering the stabilization energy for all compounds. Also, the FMO (Frontier Moleular Orbital) analyses implied that the product P2 would prefer the intermolecular interactions would rather than the intramolecular interactions. (C) 2021 Published by Elsevier B.V.
dc.description.sponsorshipEC Research Innovation Action under the H2020 Programme [HPC17ZF3B6]; Ibon Alkorta [Instituto De Quimica Medica (CSIC), Theoretical Chemisty Group]
dc.description.sponsorshipThe work has been performed under the Project HPC-EUROPA3 (HPC17ZF3B6), with the support of the EC Research Innovation Action under the H2020 Programme; in particular, the author gratefully acknowledges the support of Ibon Alkorta [Instituto De Quimica Medica (CSIC), Theoretical Chemisty Group] and the computer resources and technical support provided by [BSC center]. Also, a part of the calculations have been carried out at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid eInfrastructure).
dc.identifier.doi10.1016/j.molstruc.2021.132262
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85121904973
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2021.132262
dc.identifier.urihttps://hdl.handle.net/20.500.11776/7320
dc.identifier.volume1253
dc.identifier.wosWOS:000744752500010
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorUludağ, Nesimi
dc.institutionauthorErçağ, Erol
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.subjectCarbazoles
dc.subjectBiological activity
dc.subjectQuantum chemical calculations
dc.subjectChemical reactivity
dc.subjectDensity-Functional Theory
dc.subjectExcitation-Energies
dc.subjectBasis-Set
dc.subjectDerivatives
dc.subjectHybrid
dc.subjectSpectroscopy
dc.subjectAnticancer
dc.subjectFramework
dc.subjectHardness
dc.subjectNmr
dc.titleCyanomethylation of 2,3,4,9-tetrahydro-1H-carbazol-1-one based on using two different reagents: Antioxidant activity and DFT studies
dc.typeArticle

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