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dc.creatorValentić, Nataša V.
dc.creatorVitnik, Željko
dc.creatorMijin, Dušan
dc.creatorUšćumlić, Gordana
dc.creatorTodorović, Nina
dc.creatorJuranić, Ivan
dc.date.accessioned2020-12-08T11:38:54Z
dc.date.available2020-12-08T11:38:54Z
dc.date.issued2009
dc.identifier.issn1551-7004
dc.identifier.urihttps://cer.ihtm.bg.ac.rs/handle/123456789/3994
dc.description.abstractThe C-13 NMR chemical shifts of the C2 carbon atom in the heteroaromatic nuclei of seventeen 5-(3- and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones were determined in deuterated DMSO solution. For quantitative assessment of the substituent effects on the C-13 NMR chemical shifts simple and extended Hammett equations and Swain-Lupton equation were used. The mode of transmission of substituent effects have been discussed in a relation to the geometry of investigated molecules. The geometry data were obtained using semiempirical MNDO-PM6 energy calculations. The observed C-13 NMR substituent chemical shifts were correlated with literature C-13 NMR data for the corresponding 3- and 4-substituted- 2',6'-dimethylazobenzenes and 3- and 4-substituted azobenzenes. A good linear dependence obtained in this way, provided a basis to discuss the influence of the ortho-methyl groups on the degree of coplanarity of azobenzene and pyridone systems, and on the efficiency of transmission of electronic substituent effect from one ring to the other one.en
dc.language.isoensr
dc.publisherArkat USA Inc.sr
dc.relationinfo:eu-repo/grantAgreement/MESTD/MPN2006-2010/142063/RS//sr
dc.relationinfo:eu-repo/grantAgreement/MESTD/MPN2006-2010/142010/RS//sr
dc.rightsopenAccesssr
dc.sourceARKIVOC - Online Journal of Organic Chemistrysr
dc.subjectLFER modelssr
dc.subjectarylazo pyridone dyessr
dc.subjectsubstituent effectssr
dc.subjectazo linking groupsr
dc.subjectMNDO-PM6sr
dc.subjectDFT-ab initio calculationssr
dc.subjectuv/vis absorption-spectrasr
dc.subjecthindered azobenzenessr
dc.subjectazo dyessr
dc.subjectpm3sr
dc.subjectsubstituentsr
dc.subjectmechanismsr
dc.subjectsolventssr
dc.titleLinear Free Energy Relationships of the C-13 NMR chemical shifts in 5-(3-and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridonesen
dc.typearticlesr
dc.rights.licenseBYsr
dcterms.abstractЈуранић, Иван; Валентић, Наташа В.; Витник, Жељко; Ушћумлић, Гордана; Тодоровић, Нина; Мијин, Душан;
dc.rights.holderThe Authorssr
dc.citation.volume2009
dc.citation.issue13
dc.citation.spage227
dc.citation.epage240
dc.citation.rankM23
dc.identifier.doi10.3998/ark.5550190.0010.d20
dc.identifier.fulltexthttp://cer.ihtm.bg.ac.rs/bitstream/id/18387/linear-free-energy-relationships-of-the-13c-nmr-chemical.pdf
dc.identifier.scopus2-s2.0-77953199233
dc.identifier.wos000277913200020
dc.type.versionpublishedVersionsr


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