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Effect of substituents on the 13C-NMR chemical shifts of 3-methylene-4-substituted-1, 4-pentadienes - Part I
Efekti supstituenata na 13C-NMR hemijska pomeranja 3-metilen-4-supstituisanih-1,4-pentadiena - deo I
dc.creator | Valentić, Nataša | |
dc.creator | Vitnik, Željko | |
dc.creator | Kozhushkov, Sergei I. | |
dc.creator | de Majere, Armin | |
dc.creator | Ušćumlić, Gordana | |
dc.creator | Juranić, Ivan | |
dc.date.accessioned | 2021-03-10T10:09:40Z | |
dc.date.available | 2021-03-10T10:09:40Z | |
dc.date.issued | 2003 | |
dc.identifier.issn | 0352-5139 | |
dc.identifier.uri | http://TechnoRep.tmf.bg.ac.rs/handle/123456789/574 | |
dc.description.abstract | The principles of linear free energy relationships were applied to the 13C substituent chemical shifts (SCS) of the carbon atoms in the unsaturated chain of 3-methylene-4-substituted-1,4-pentadienes. Correlations of the SCS with the substituent parameters of Swain and Lupton provide a mutually consistent picture of the electronic effects in these compounds. The pattern of the electronic effects can be fully rationalized by a model based on the direct transmission of substituent effects through-space (direct through-space field effects), and via conjugative interactions (resonance effects), or by substituent-induced polarization of the ¶-system in the unsaturated chain (¶-polarization effect). Semi-empirical MNDO-PM3 calculations suggest the s-cis conformation of 3-methylene-4-substituted-1,4-pentadienes as the one with minimal heat of formation. | en |
dc.description.abstract | Na 13C supstituentska hemijska pomeranja (SHP) ugljenikovih atoma u nezasićenom lancu 3-metilen-4-supstituisanih-1,4-pentadiena su primenjeni principi linearne korelacije slobodne energije. Korelacije SHP sa supstituentskim parametrima Swain-a i Lupton-a pružaju usaglašenu sliku elektronskih efekata u ovim jedinjenjima. Koncept elektronskih efekata može u potpunosti biti objašnjen modelom koji se zasniva na direktnom prenošenju efekata supstituenata kroz prostor (direktni efekti polja kroz prostor) i preko konjugacionih interakcija (rezonancioni efekti), ili putem supstituentom izazvane polarizacije ¶-sistema u nezasićenom lancu (efekti ¶-polarizacije). MNDO-PM3 semiempirijska izračunavanja upućuju na s-cis konformaciju 3-metilen-4-supstituisanih-1,4-pentadiena kao konformaciju sa minimalnom energijom obrazovanja. | sr |
dc.publisher | Serbian Chemical Society, Belgrade | |
dc.rights | openAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.source | Journal of the Serbian Chemical Society | |
dc.subject | [3]dendralenes | en |
dc.subject | unsaturated chain carbon 13C SCS | en |
dc.subject | substituent effects | en |
dc.subject | reverse 13C SCS effect | en |
dc.subject | MNDO-PM3 calculations | en |
dc.title | Effect of substituents on the 13C-NMR chemical shifts of 3-methylene-4-substituted-1, 4-pentadienes - Part I | en |
dc.title | Efekti supstituenata na 13C-NMR hemijska pomeranja 3-metilen-4-supstituisanih-1,4-pentadiena - deo I | sr |
dc.type | article | |
dc.rights.license | BY-NC-ND | |
dc.citation.epage | 76 | |
dc.citation.issue | 2 | |
dc.citation.other | 68(2): 67-76 | |
dc.citation.rank | M23 | |
dc.citation.spage | 67 | |
dc.citation.volume | 68 | |
dc.identifier.fulltext | http://TechnoRep.tmf.bg.ac.rs/bitstream/id/11097/0352-51390302067V.pdf | |
dc.identifier.rcub | https://hdl.handle.net/21.15107/rcub_technorep_574 | |
dc.identifier.scopus | 2-s2.0-0037246422 | |
dc.identifier.wos | 000181696700001 | |
dc.type.version | publishedVersion |