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Ring- and side-group conformational properties of di-O-acylated xylopyranosides: A computational study
dc.creator | Vitnik, Željko | |
dc.creator | Fabian, Walter M F | |
dc.date.accessioned | 2019-01-30T17:46:08Z | |
dc.date.available | 2019-01-30T17:46:08Z | |
dc.date.issued | 2015 | |
dc.identifier.issn | 2210-271X | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/1746 | |
dc.description.abstract | The conformational properties (C-4(1), C-1(4), and skew ring structures, side chain torsion) of methyl 2,4-(1) and 3,4-O-diacetyl (2) as well as 2,4-(3) and 3,4-O-dibenzoyl (4)-SS-D-xylopyranoside are calculated by dispersion-corrected density functional theory (B3LYP-D3) and LPNO-CEPA/1-def2-TZVPP. Derivatives with acyl groups in positions 2 and 4 (1 and 3) prefer the 1C4 chair conformation of the pyranose chair; 3,4-di-O-acyl compounds 2 and 4 show nearly equal or even dominating amounts of the C-4(1) chair. Intramolecular hydrogen bonding of the type O3-H center dot center dot O1 (1 and 3) and O2-H center dot center dot center dot O4 are characteristic for the lowest energy conformations of 1C4 chairs. With increasing solvent polarity a shift towards 4C1 chair structures is calculated. B3LYP-D3 conformer populations show fairly good agreement with CEPA/1 results (R-2 = 0.992). | en |
dc.publisher | Elsevier | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172035/RS// | |
dc.rights | restrictedAccess | |
dc.source | Computational and Theoretical Chemistry | |
dc.subject | Density functional | en |
dc.subject | Dispersion correction | en |
dc.subject | LPNO-CEPA/1 | en |
dc.subject | Ring conformation | en |
dc.subject | Substituent and solvent effect | en |
dc.title | Ring- and side-group conformational properties of di-O-acylated xylopyranosides: A computational study | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Фабиан, Wалтер М Ф; Витник, Жељко; | |
dc.citation.volume | 1051 | |
dc.citation.spage | 104 | |
dc.citation.epage | 109 | |
dc.citation.other | 1051: 104-109 | |
dc.citation.rank | M23 | |
dc.identifier.doi | 10.1016/j.comptc.2014.11.004 | |
dc.identifier.scopus | 2-s2.0-84919343344 | |
dc.identifier.wos | 000347862000013 | |
dc.type.version | publishedVersion |