Direct arylation of heteroarenes by PEPPSI-type palladium-NHC complexes and representative quantum chemical calculations for the compound which the structure was determined by X-ray crystallography

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dc.authoridÖzdemir, İsmail/0000-0001-6325-0216
dc.authoridDüşünceli, Serpil Demir/0000-0001-8765-4039
dc.authoridTahir, Muhammad Nawaz/0000-0002-6815-9806;
dc.authorwosidŞAHİN, Neslihan/F-6402-2019
dc.authorwosidÖzdemir, İsmail/ABI-5192-2020
dc.authorwosidSerdaroğlu, Goncagül/ADT-1750-2022
dc.authorwosidDemir, Serpil/AAI-1740-2019
dc.authorwosidDüşünceli, Serpil Demir/AAA-7160-2021
dc.authorwosidTahir, Muhammad Nawaz/HPB-5726-2023
dc.authorwosidSerdaroğlu, Goncagül/I-6780-2016
dc.contributor.authorSahin, Neslihan
dc.contributor.authorSerdaroglu, Goncagul
dc.contributor.authorDusunceli, Serpil Demir
dc.contributor.authorTahir, Muhammad Navaz
dc.contributor.authorArici, Cengiz
dc.contributor.authorOzdemir, Ismail
dc.date.accessioned2024-08-04T20:46:56Z
dc.date.available2024-08-04T20:46:56Z
dc.date.issued2019
dc.departmentİnönü Üniversitesien_US
dc.description.abstractIn this study, we synthesized five new PEPPSI-type Pd-NHC complexes with high yields around 78-83%. The structures of all complexes were characterized by FT-IR, H-1 NMR, and C-13{H-1} NMR spectroscopies. Further, the structure of 2c was determined by X-ray crystallography. The single-crystal structure of 2c shows that coordination geometry around Pd is distorted square planar. The Pd-NHC complexes were efficient catalysts for the direct C5-arylation of 2-n-butylthiazole, 2-n-butylfuran, and 2-n-butylthiophene with various aryl-bromides and showed high catalytic activity for arylation reaction using only 1 mol% catalyst loading at 130 degrees C for 1 h. The conversions for substrates containing electron-withdrawing groups were higher than for substituents containing electron-donating groups. In order to evaluate the catalytic activity of the complexes, representative electronic and spectroscopic simulations by DFT method have been performed for 2c. NBO analysis has revealed that the strongest interaction contributing to the lowering of the molecular stabilization energy for 2c is predicted as pi(C11-N27) -> pi*(N26-C28) with E-(2) = 73.93 kcal mol(-1). In addition, FMO analysis has implied that 2c is more chemically reactive because of its lower energy gap value. According to the other quantum chemical parameters, 2c is softer, better electrophile and has more charge-transfer capability than 1c.en_US
dc.description.sponsorshipSivas Cumhuriyet University, Scientific Research Projects Department [CUBAP: EGT-066]en_US
dc.description.sponsorshipThis work was supported by Sivas Cumhuriyet University, Scientific Research Projects Department (Project No: CUBAP: EGT-066). All calculations have been carried out at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure).en_US
dc.identifier.doi10.1080/00958972.2019.1692202
dc.identifier.endpage3284en_US
dc.identifier.issn0095-8972
dc.identifier.issn1029-0389
dc.identifier.issue19-21en_US
dc.identifier.scopus2-s2.0-85075389114en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage3258en_US
dc.identifier.urihttps://doi.org/10.1080/00958972.2019.1692202
dc.identifier.urihttps://hdl.handle.net/11616/99064
dc.identifier.volume72en_US
dc.identifier.wosWOS:000498087900001en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherTaylor & Francis Ltden_US
dc.relation.ispartofJournal of Coordination Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectPEPPSIen_US
dc.subjectN-heterocyclic carbineen_US
dc.subjectX-ray structureen_US
dc.subjectdirect arylationen_US
dc.subjectquantum chemical calculationsen_US
dc.titleDirect arylation of heteroarenes by PEPPSI-type palladium-NHC complexes and representative quantum chemical calculations for the compound which the structure was determined by X-ray crystallographyen_US
dc.typeArticleen_US

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