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dc.creatorVitnik, Željko
dc.creatorFabian, Walter M F
dc.date.accessioned2019-01-30T17:46:08Z
dc.date.available2019-01-30T17:46:08Z
dc.date.issued2015
dc.identifier.issn2210-271X
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/1746
dc.description.abstractThe 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.publisherElsevier Science Bv, Amsterdam
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172035/RS//
dc.rightsrestrictedAccess
dc.sourceComputational and Theoretical Chemistry
dc.subjectDensity functionalen
dc.subjectDispersion correctionen
dc.subjectLPNO-CEPA/1en
dc.subjectRing conformationen
dc.subjectSubstituent and solvent effecten
dc.titleRing- and side-group conformational properties of di-O-acylated xylopyranosides: A computational studyen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractФабиан, Wалтер М Ф; Витник, Жељко;
dc.citation.volume1051
dc.citation.spage104
dc.citation.epage109
dc.citation.other1051: 104-109
dc.citation.rankM23
dc.identifier.doi10.1016/j.comptc.2014.11.004
dc.identifier.rcubConv_3269
dc.identifier.scopus2-s2.0-84919343344
dc.identifier.wos000347862000013
dc.type.versionpublishedVersion


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