A novel synthesis of octahydropyrido[3,2-c]carbazole framework of aspidospermidine alkaloids and a combined computational, FT-IR, NMR, NBO, NLO, FMO, MEP study of the cis-4a-Ethyl-1(2hydroxyethyl)-2,3,4,4a,5,6,7,11c-octahydro-1H-pyrido[3,2-c] carbazole

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dc.authorid0000-0002-2819-3612
dc.authorid0000-0001-7649-9168
dc.authorscopusid6507868758
dc.authorscopusid36447801100
dc.authorscopusid57194470624
dc.authorwosidSerdaroğlu, Goncagül/I-6780-2016
dc.authorwosiduludag, Nesimi/AAB-1353-2020
dc.contributor.authorUludağ, Nesimi
dc.contributor.authorSerdaroğlu, Goncagül
dc.contributor.authorYinanç, Abdullah
dc.date.accessioned2022-05-11T14:15:38Z
dc.date.available2022-05-11T14:15:38Z
dc.date.issued2018
dc.departmentFakülteler, Fen Edebiyat Fakültesi, Kimya Bölümü
dc.departmentMeslek Yüksekokulları, Teknik Bilimler Meslek Yüksekokulu, İnşaat Bölümü
dc.description.abstractIn this study, we performed a novel synthesis of the octahydropyrido[3,2-c]carbazole derivative 6 from 1 in five steps with a 34% overall yield. We also developed a unique compound 2 by a cyclization reaction from the cyanoethylation of compound 1, which is an intermediate step in the synthesis of Aspidospermidine. The parent compound of Aspidospermidine alkaloids, comprise a large family of diverse structures. As a result, we obtained octahydropyrido[3,2-c]carbazole (6)and the proposed method may be applicable to other alkaloids. All quantum chemical calculations of the cis-4a-Ethyl-1-(2-hydroxyethyl)-2,3,4,4a,5,6,7,11c-octahydro-1H-pyrido[3,2-c]carbazole have been performed with the DFT/B3LYP and HF methods by using the Gaussian 09W software package. The most stable conformer obtained from the Potential Energy Surface (PES) scan analysis at the B3LYP/6-31G** level of theory in the gas phase was used as the starting structure of the title compound to further computational analysis. The Natural Bond Orbital (NBO) and NLO analyses were performed to evaluate the intra-molecular interactions contributing to the molecular stability and to predict the optical properties of the title compound, respectively. Gauge-Independent Atomic Orbital (GIAO) approach was used to determine the H-1 and C-1 NMR chemical shifts of the title compound by subtracting the shielding constants of TMS at both methods. The calculated vibrational frequencies of the title compound were assigned by using the VEDA program and were scaled down by using the scaling factor 0.9668 for B3LYP/6-311++G(d, p) and 0.9050 for HF/6-311++G(d, p) to improve the calculated vibrational frequencies. The FMO (frontier molecular orbital) analysis was evaluated to predict the chemical and physical properties of the title compound and the HOMO, LUMO, and MEP diagrams were visualized by GaussView 4.1 program to present the reactive site of the title compound. (C) 2018 Elsevier B.V. All rights reserved.
dc.description.sponsorshipNamik Kemal University Scientific Research projects Coordination DepartmentNamik Kemal University [NKUBAP. 00.10YL.14.06]; Cumhuriyet University scientific research projects departmentCumhuriyet University [CUBAP: EGT-066]
dc.description.sponsorshipThis investigation was supported by a grant from Namik Kemal University Scientific Research projects Coordination Department (Project No. NKUBAP. 00.10YL.14.06) and by the Cumhuriyet University scientific research projects department (Project No. CUBAP: 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.2018.02.046
dc.identifier.endpage168
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85042234650
dc.identifier.scopusqualityQ2
dc.identifier.startpage152
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2018.02.046
dc.identifier.urihttps://hdl.handle.net/20.500.11776/6000
dc.identifier.volume1161
dc.identifier.wosWOS:000428972900018
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorUludağ, Nesimi
dc.institutionauthorYinanç, Abdullah
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.subjectAspidospermidine
dc.subjectOctahydropyrido[3,2-c]carbazole
dc.subjectDeethylaspidospermidine
dc.subjectNBO
dc.subjectNLO
dc.subjectMEP
dc.subjectConcise Total-Synthesis
dc.subjectAb-Initio Hf
dc.subject1st-Order Hyperpolarizability
dc.subjectMolecular-Structure
dc.subjectHomo-Lumo
dc.subjectIndole Alkaloids
dc.subjectFormal Synthesis
dc.subjectRecent Progress
dc.subjectUv
dc.subjectRaman
dc.titleA novel synthesis of octahydropyrido[3,2-c]carbazole framework of aspidospermidine alkaloids and a combined computational, FT-IR, NMR, NBO, NLO, FMO, MEP study of the cis-4a-Ethyl-1(2hydroxyethyl)-2,3,4,4a,5,6,7,11c-octahydro-1H-pyrido[3,2-c] carbazole
dc.typeArticle

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