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Korelaciona analiza IR, 1H- i 13C-NMR spektalnih podataka N-alkil- i N-cikloalkilcijanoacetamida

dc.creatorMarinković, Aleksandar
dc.creatorNedeljković, Jelena
dc.creatorMijin, Dušan
dc.creatorIlić, Nataša
dc.creatorPetrović, Slobodan
dc.date.accessioned2021-03-10T11:32:32Z
dc.date.available2021-03-10T11:32:32Z
dc.date.issued2011
dc.identifier.issn1451-9372
dc.identifier.urihttp://TechnoRep.tmf.bg.ac.rs/handle/123456789/1847
dc.description.abstractLinear free energy relationships (LFER) were applied to the IR, 1H- and 13C- -NMR spectral data in N-alkyl and N-cycloalkyl cyanoacetamides. N-alkyl and N-cycloalkyl cyanocetamides were synthesized from corresponding amine and ethyl cyanoacetate. A number of substituents were employed for alkyl substitution, and fairly good correlations were obtained, using simple Hammett equation. In N-alkyl and N-cycloalkyl cyanoacetamides substituent cause SCS of N-H hydrogen primarily by steric interaction, polar subtituent effect influences SCS shift of C=O carbon, while steric effect of N-alkyl substituent causes IR stretching frequencies of N-H, C=O and CN group. The conformations of investigated compounds have been studied by the use of semiempirical PM6 method, and together with LFER analysis, give a better insight into the influence of such a structure on the transmission of electronic substituent effects. Negative ρ values for several correlations (reverse substituent effect) were found.en
dc.description.abstractPrincipi linearnih korelacija slobodnih energija (LFER) su primenjeni na IR, 1H- i 13C-NMR spektralne podatke N-alkil i N-cikloalkilcijanoacetamida. Širok opseg alkil i cikloalkil suptituenata je korišćen pri sintezi N-alkil i N-cikloalkilcijanoacetamida sa ciljem ispitivanja uticaja njihovih elektronskih i sternih efekata na IR, 1H i 13C NMR spektralne podatke. Zadovoljavajuće korelacije su dobijene primenom proste Hammett-ove jednačine. Na osnovu korelacionih rezultata uočen je primaran uticaj sternih efekata supstituenata na SCS (supstituent indukovana hemijska pomeranja) vrednosti N-H vodonika ispitivanih jedinjenja, što je posledica blizine i različitih konformacija N-alkil i N-cikloalkil supstituenata. Takođe se uočava reversni efekat supstituenata na SCS pomeranja karbonilnog C=O ugljenika, kao posledica π-polarizacije. Indukovani dipol na N-alkil ili N-cikloalkil supstituentu izaziva povećanje elektronske gustine karbonilnog ugljenika iako elektron-akceptorski efekat supstituenta raste. Može se zaključiti da se efekat π-polarizacije odražava na veličinu rezonancionog efekta amidne grupe. Polarni efekat N-alkil ili N-cikloalkil supstituenata se primarno prenosi efektom polja kroz prostor. Uticaj efekata N-alkil ili N-cikloalkil supstituenata na IR vibracije istezanja N-H (simetrične i antisimetrične), C=O i CN veze je prevashodno određen konformacionim (sternim) efektom supstituenata koji utiče na jačinu veze, a time i na položaj trake u odgovarajućem spektru.sr
dc.publisherAssociation of the Chemical Engineers of Serbia
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172013/RS//
dc.rightsopenAccess
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/
dc.sourceChemical Industry & Chemical Engineering Quarterly
dc.subjectN-alkyl cyanoacetamidesen
dc.subjectN-cycloalkyl cyanoacetamideen
dc.subjectLFER analysisen
dc.subjectIR and NMR spectraen
dc.subjectSCS shiften
dc.subjectHammett equationen
dc.subjectN-alkilcijanoacetamidisr
dc.subjectN-cikloalkilcijanoacetamidisr
dc.subjectLFER analizasr
dc.subjectIR i NMR spektrisr
dc.subjectSCS pomerajsr
dc.subjectHammett-ova jednačinasr
dc.titleCorrelation analysis of IR, 1H- and 13C-NMR spectral data of N-alkyl and N-cycloalkyl cyanoacetamidesen
dc.titleKorelaciona analiza IR, 1H- i 13C-NMR spektalnih podataka N-alkil- i N-cikloalkilcijanoacetamidasr
dc.typearticle
dc.rights.licenseBY-NC-ND
dc.citation.epage314
dc.citation.issue3
dc.citation.other17(3): 307-314
dc.citation.rankM23
dc.citation.spage307
dc.citation.volume17
dc.identifier.doi10.2298/CICEQ110302016M
dc.identifier.fulltexthttp://TechnoRep.tmf.bg.ac.rs/bitstream/id/8676/1451-93721100016M.pdf
dc.identifier.scopus2-s2.0-80052873985
dc.identifier.wos000296947800007
dc.type.versionpublishedVersion


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