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dc.contributor.authorHaşlak, Zeynep Pınar
dc.contributor.authorÇinar, Sesil Agopcan
dc.contributor.authorSarigul, Sevgi
dc.contributor.authorMonard, Gerald
dc.contributor.authorDoğan, İlknur
dc.contributor.authorAviyente, Viktorya
dc.date.accessioned2021-06-05T19:56:16Z
dc.date.available2021-06-05T19:56:16Z
dc.date.issued2020
dc.identifier.issn1477-0520
dc.identifier.issn1477-0539
dc.identifier.urihttps://doi.org/10.1039/c9ob02556a
dc.identifier.urihttps://hdl.handle.net/20.500.12960/224
dc.description0000-0001-9430-4096en_US
dc.description0000-0002-2850-9816en_US
dc.description0000-0002-3378-3481en_US
dc.description0000-0002-0676-2415en_US
dc.descriptionPubMed: 32022073en_US
dc.descriptionWOS:000526592300018en_US
dc.description.abstractRecently, Sarigul and Dogan have synthesized a number of enantiomerically enriched axially chiral atropoisomeric 2-thiohydantoins by the reaction of c-amino acid ester salts and o-aryl isothiocyanates in the presence of triethyl amine (TEA) in dichloromethane. The non-axially chiral derivative 5-methyl-3-phenyl-2-thiohydantoin gave a racemic product whereas the axially chiral 5-methyl-3-o-bromophenyl-2-thiohydantoin was less prone to racemize at C-5 of the heterocyclic ring. In this study, we present a computational study (M06-2X/6-311-1-G(d,p) for C, H, O, N and S. M06-2X/6-3111 IG(3df,3pd) for Br) in order to propose plausible mechanisms for the racemization and cyclization steps for 2-thiohydantoin derivatives. The study includes rationalization based on steric as well as the electrostatic effects to elucidate the ep merization differences at C-5.en_US
dc.description.sponsorshipNational Center for High Performance Computing at Istanbul Technical UniversityIstanbul Technical University [5004092016]; Bogazici University Research Fund (BAP)Bogazici University [16241]en_US
dc.description.sponsorshipComputational resources were provided by the National Center for High Performance Computing at Istanbul Technical University (Grant number 5004092016) funded by Bogazici University Research Fund (BAP) with Grant Number 16241.en_US
dc.language.isoengen_US
dc.publisherRoyal Soc Chemistryen_US
dc.relation.ispartofOrganic & Biomolecular Chemistryen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject[No Keywords]en_US
dc.titleElucidation of the atroposelectivity in the synthesis of axially chiral thiohydantoin derivativesen_US
dc.typearticleen_US
dc.authorid0000-0002-2850-9816
dc.departmentFen Edebiyat Fakültesi, Kimya Bölümüen_US
dc.department-temp[Haslak, Zeynep Pinar; cinar, Sesil Agopcan; Dogan, Ilknur; Aviyente, Viktorya] Bogazici Univ, Dept chem, TR-34342 Istanbul, Turkey; [Haslak, Zeynep Pinar; Monard, Gerald] Univ Lorraine, cNRS, LPcT, F-54000 Nancy, France; [Haslak, Zeynep Pinar] Piri Reis Univ, Fac Sci & Letters, TR-34940 Istanbul, Turkey; [Sarigul, Sevgi] Acibadem Mehmet Ali Aydinlar Univ, Fac Pharm, TR-34752 Istanbul, Turkeyen_US
dc.contributor.institutionauthorHaşlak, Zeynep Pınar
dc.identifier.doi10.1039/c9ob02556a
dc.identifier.volume18en_US
dc.identifier.issue12en_US
dc.identifier.startpage2233en_US
dc.identifier.endpage2241en_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US


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