Plausible Pnicogen Bonding of epi-Cinchonidine as a Chiral Scaffold in Catalysis
DC Field | Value | Language |
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dc.contributor.author | Ullah, Zakir | - |
dc.contributor.author | Kim, Kang | - |
dc.contributor.author | Venkanna, Arramshetti | - |
dc.contributor.author | Kim, Hye Su | - |
dc.contributor.author | Kim, Moon Il | - |
dc.contributor.author | Kim, Mi-hyun | - |
dc.date.accessioned | 2021-07-28T00:41:19Z | - |
dc.date.available | 2021-07-28T00:41:19Z | - |
dc.date.created | 2021-07-28 | - |
dc.date.issued | 2021-07-06 | - |
dc.identifier.issn | 2296-2646 | - |
dc.identifier.uri | https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/81764 | - |
dc.description.abstract | As a non-covalent interaction of a chiral scaffold in catalysis, pnicogen bonding of epi-cinchonidine (epi-CD), a cinchona alkaloid, was simulated to consider whether the interaction can have the potential controlling enantiotopic face like hydrogen bonding. Among five reactive functional groups in epi-CD, two stable complexes of the hydroxyl group (X-epi-CD1) at C-17 and of the quinoline ring (X-epi-CD2) at N-16 with pnictide family analytes [X = substituted phosphine (PX), i.e., F, Br, Cl, CF3, CN, HO, NO2, and CH3, and pnictide family analytes, i.e., PBr3, BiI3, SbI3, and AsI3] were predicted with intermolecular interaction energies, charge transfer (Q(Mulliken) and Q(NBO)), and band gap energies of HOMO-LUMO (Eg) at the B3LYP/6-31G(d,p) level of density functional theory. It was found that the dominant site of pnicogen bonding in epi-CD is the quinoline ring (N-16 atom) rather than the hydroxyl group (O-36 atom). In addition, the UV-Vis spectra of the complex were calculated by time-dependent density functional theory (TD-DFT) at the B3LYP/6-31+G(d,p) level and compared with experimental measurements. Through these calculations, two intermolecular interactions (H-bond vs. pnicogen bond) of epi-CD were compared. | - |
dc.language | 영어 | - |
dc.language.iso | en | - |
dc.publisher | FRONTIERS MEDIA SA | - |
dc.relation.isPartOf | FRONTIERS IN CHEMISTRY | - |
dc.title | Plausible Pnicogen Bonding of epi-Cinchonidine as a Chiral Scaffold in Catalysis | - |
dc.type | Article | - |
dc.type.rims | ART | - |
dc.description.journalClass | 1 | - |
dc.identifier.wosid | 000674598300001 | - |
dc.identifier.doi | 10.3389/fchem.2021.669515 | - |
dc.identifier.bibliographicCitation | FRONTIERS IN CHEMISTRY, v.9 | - |
dc.description.isOpenAccess | N | - |
dc.identifier.scopusid | 2-s2.0-85110669175 | - |
dc.citation.title | FRONTIERS IN CHEMISTRY | - |
dc.citation.volume | 9 | - |
dc.contributor.affiliatedAuthor | Ullah, Zakir | - |
dc.contributor.affiliatedAuthor | Kim, Kang | - |
dc.contributor.affiliatedAuthor | Venkanna, Arramshetti | - |
dc.contributor.affiliatedAuthor | Kim, Hye Su | - |
dc.contributor.affiliatedAuthor | Kim, Moon Il | - |
dc.contributor.affiliatedAuthor | Kim, Mi-hyun | - |
dc.type.docType | Article | - |
dc.subject.keywordAuthor | pnicogen bonding | - |
dc.subject.keywordAuthor | DFT calculation | - |
dc.subject.keywordAuthor | enantiotopic face | - |
dc.subject.keywordAuthor | HOMO-LUMO | - |
dc.subject.keywordAuthor | UV-Vis spectroscopy | - |
dc.subject.keywordPlus | ASYMMETRIC MICHAEL ADDITION | - |
dc.subject.keywordPlus | ENANTIOSELECTIVE CONJUGATE ADDITION | - |
dc.subject.keywordPlus | CONFORMATIONAL STABILIZER | - |
dc.subject.keywordPlus | ORGANOCATALYTIC SYNTHESIS | - |
dc.subject.keywordPlus | NONCOVALENT INTERACTIONS | - |
dc.subject.keywordPlus | AROMATIC THIOLS | - |
dc.subject.keywordPlus | O INTERACTION | - |
dc.subject.keywordPlus | COMBINED NMR | - |
dc.subject.keywordPlus | ANION-PI | - |
dc.subject.keywordPlus | HALOGEN | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
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