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dc.creatorBaranac-Stojanović, Marija
dc.creatorStojanović, Milovan
dc.date.accessioned2019-01-30T17:36:25Z
dc.date.available2019-01-30T17:36:25Z
dc.date.issued2013
dc.identifier.issn0022-3263
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/1284
dc.description.abstractThis study was undertaken in order to rationalize the peculiar H-1 NMR chemical shifts of cyclopropane (delta 0.22) and cyclobutane (delta 1.98) which are shifted upfield and downfield with respect to larger cycloalkanes (delta 1.44-1.54). This is conventionally accounted for by shielding contributions arising from an aromatic-like ring current in cyclopropane, involving six electrons in the three C-C bonds, and deshielding coming from the sigma antiaromatic CC framework of cyclobutane. The shielding pattern arising from the cyclopropane and cyclobutane CC framework response to a perpendicular magnetic field was visualized as two-dimensional grid distribution of NICS values. Further insight into the origin of chemical shift values was obtained by the NCS-NBO analysis of proton shielding tensor. In the case of cyclopropane, the CC framework shielding pattern implies the existence of both delocalized and localized currents that have a dominant shielding effect on protons. The magnitude of C-H bonds shielding effect is significant, too. Unlike the conventional interpretation, the CC framework shields cyclobutane hydrogens, and its response to a perpendicular magnetic field is quite similar to responses of other planar sigma CC frameworks.en
dc.publisherAmer Chemical Soc, Washington
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172020/RS//
dc.rightsrestrictedAccess
dc.sourceJournal of Organic Chemistry
dc.titleH-1 NMR Chemical Shifts of Cyclopropane and Cyclobutane: A Theoretical Studyen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractБаранац-Стојановиц, Марија; Стојановић, Милован;
dc.citation.volume78
dc.citation.issue4
dc.citation.spage1504
dc.citation.epage1507
dc.citation.other78(4): 1504-1507
dc.citation.rankM21
dc.identifier.pmid23330566
dc.identifier.doi10.1021/jo3025863
dc.identifier.rcubConv_2932
dc.identifier.scopus2-s2.0-84873955750
dc.identifier.wos000315254100019
dc.type.versionpublishedVersion


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