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Correlation analysis of IR, 1H- and 13C-NMR spectral data of N-alkyl and N-cycloalkyl cyanoacetamides
Korelaciona analiza IR, 1H- i 13C-NMR spektalnih podataka N-alkil- i N-cikloalkilcijanoacetamida
dc.creator | Marinković, Aleksandar | |
dc.creator | Nedeljković, Jelena | |
dc.creator | Mijin, Dušan | |
dc.creator | Ilić, Nataša | |
dc.creator | Petrović, Slobodan | |
dc.date.accessioned | 2021-03-10T11:32:32Z | |
dc.date.available | 2021-03-10T11:32:32Z | |
dc.date.issued | 2011 | |
dc.identifier.issn | 1451-9372 | |
dc.identifier.uri | http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1847 | |
dc.description.abstract | Linear 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.abstract | Principi 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.publisher | Association of the Chemical Engineers of Serbia | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172013/RS// | |
dc.rights | openAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.source | Chemical Industry & Chemical Engineering Quarterly | |
dc.subject | N-alkyl cyanoacetamides | en |
dc.subject | N-cycloalkyl cyanoacetamide | en |
dc.subject | LFER analysis | en |
dc.subject | IR and NMR spectra | en |
dc.subject | SCS shift | en |
dc.subject | Hammett equation | en |
dc.subject | N-alkilcijanoacetamidi | sr |
dc.subject | N-cikloalkilcijanoacetamidi | sr |
dc.subject | LFER analiza | sr |
dc.subject | IR i NMR spektri | sr |
dc.subject | SCS pomeraj | sr |
dc.subject | Hammett-ova jednačina | sr |
dc.title | Correlation analysis of IR, 1H- and 13C-NMR spectral data of N-alkyl and N-cycloalkyl cyanoacetamides | en |
dc.title | Korelaciona analiza IR, 1H- i 13C-NMR spektalnih podataka N-alkil- i N-cikloalkilcijanoacetamida | sr |
dc.type | article | |
dc.rights.license | BY-NC-ND | |
dc.citation.epage | 314 | |
dc.citation.issue | 3 | |
dc.citation.other | 17(3): 307-314 | |
dc.citation.rank | M23 | |
dc.citation.spage | 307 | |
dc.citation.volume | 17 | |
dc.identifier.doi | 10.2298/CICEQ110302016M | |
dc.identifier.fulltext | http://TechnoRep.tmf.bg.ac.rs/bitstream/id/8676/1451-93721100016M.pdf | |
dc.identifier.scopus | 2-s2.0-80052873985 | |
dc.identifier.wos | 000296947800007 | |
dc.type.version | publishedVersion |