dc.contributor.author | Haşlak, Zeynep Pınar | |
dc.contributor.author | Çinar, Sesil Agopcan | |
dc.contributor.author | Sarigul, Sevgi | |
dc.contributor.author | Monard, Gerald | |
dc.contributor.author | Doğan, İlknur | |
dc.contributor.author | Aviyente, Viktorya | |
dc.date.accessioned | 2021-06-05T19:56:16Z | |
dc.date.available | 2021-06-05T19:56:16Z | |
dc.date.issued | 2020 | |
dc.identifier.issn | 1477-0520 | |
dc.identifier.issn | 1477-0539 | |
dc.identifier.uri | https://doi.org/10.1039/c9ob02556a | |
dc.identifier.uri | https://hdl.handle.net/20.500.12960/224 | |
dc.description | 0000-0001-9430-4096 | en_US |
dc.description | 0000-0002-2850-9816 | en_US |
dc.description | 0000-0002-3378-3481 | en_US |
dc.description | 0000-0002-0676-2415 | en_US |
dc.description | PubMed: 32022073 | en_US |
dc.description | WOS:000526592300018 | en_US |
dc.description.abstract | Recently, 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.sponsorship | National Center for High Performance Computing at Istanbul Technical UniversityIstanbul Technical University [5004092016]; Bogazici University Research Fund (BAP)Bogazici University [16241] | en_US |
dc.description.sponsorship | Computational 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.iso | eng | en_US |
dc.publisher | Royal Soc Chemistry | en_US |
dc.relation.ispartof | Organic & Biomolecular Chemistry | en_US |
dc.rights | info:eu-repo/semantics/closedAccess | en_US |
dc.subject | [No Keywords] | en_US |
dc.title | Elucidation of the atroposelectivity in the synthesis of axially chiral thiohydantoin derivatives | en_US |
dc.type | article | en_US |
dc.authorid | 0000-0002-2850-9816 | |
dc.department | Fen Edebiyat Fakültesi, Kimya Bölümü | en_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, Turkey | en_US |
dc.contributor.institutionauthor | Haşlak, Zeynep Pınar | |
dc.identifier.doi | 10.1039/c9ob02556a | |
dc.identifier.volume | 18 | en_US |
dc.identifier.issue | 12 | en_US |
dc.identifier.startpage | 2233 | en_US |
dc.identifier.endpage | 2241 | en_US |
dc.relation.publicationcategory | Makale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı | en_US |