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Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones
Sinteza i ispitivanje efekta rastvarača na UV spektre 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona
dc.creator | Mijin, Dušan | |
dc.creator | Ušćumlić, Gordana | |
dc.creator | Valentić, Nataša | |
dc.date.accessioned | 2021-03-10T09:57:45Z | |
dc.date.available | 2021-03-10T09:57:45Z | |
dc.date.issued | 2001 | |
dc.identifier.issn | 0352-5139 | |
dc.identifier.uri | http://TechnoRep.tmf.bg.ac.rs/handle/123456789/390 | |
dc.description.abstract | A number of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones from cyanoacetamide and the corresponding alkyl ethyl acetoacetates were synthesized according to modified literature procedures. The alkyl ethyl acetoacetates were obtained by the reaction of C-alkylation of ethyl acetoacetate. An investigation of the reaction conditions for the synthesis of 4-methyl-3-cyano-6-hydroxy-2-pyridone from cyanoacetamide and ethyl acetoacetate in eight different solvents was also performed. The ultraviolet absorption spectra of synthesized pyridones were measured in nine different solvents in the range 200-400 nm. The effects of solvent polarity and hydrogen bonding on the absorption spectra are interpreted by means of linear solvation energy relationships using a general equation of the form ν = νo + sπ*+aα+ bβ, where π* is a measure of the solvent polarity, α is the scale of the solvent hydrogen bond donor acidities and β is the scale of the solvent hydrogen bond acceptor basicities. . | en |
dc.description.abstract | U okviru rada je izvršena sinteza 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona iz cijanoacetamida i alkiletilacetacetata u prisustvu kalijum-hidroksida u metanolu kao rastvaraču. Alkiletilacetacetati su dobijeni reakcijom C-alkilovanja etilacetacetata odgovarajućim alkilhaloghenidima. Takođe je izvršeno ispitivanje reakcionih uslova za sintezu 4-metil-3-cijano-6-hidroksi-2-piridona iz cijanoacetamida i etilacetacetata u prisustvu KOH, NaOH i K2CO3 u različitim rastvaračima. IR, 1H-NMR i UV podaci su dati za sintetizovane piridone, a IR i 1H-NMR podaci su dati za sintetizovane alkiletilacetacetate. Apsorpcioni spektri 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona su određeni u devet rastvarača različitih polarnosti u opsegu 200-400 nm. Uticaj polarnosti rastvarača kao i efekat vodonične veze proučavani su metodom linearne korelacije solvatacionih efekata odnosno jednačinom oblika ν = νo + sπ* + aα + bβ, u kojoj je ν apsorpciona frekvenca, π* mera efekata solvatacije vezana za polarnost rastvarača, α mera uspostavljanja vodonične veze sa proton-donorskim rastvaračima, a β mera vodonične veze ostvarene sa proton-akceptorskim rastvaračima. . | 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 | alkylation | en |
dc.subject | ethyl acetoacetate | en |
dc.subject | alkyl ethyl acetoacetates synthesis | en |
dc.subject | 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones | en |
dc.subject | spectroscopy | en |
dc.subject | cyclization | en |
dc.subject | ultraviolet absorption spectra | en |
dc.subject | solvent effects | en |
dc.subject | linear solvation energy relationships | en |
dc.title | Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones | en |
dc.title | Sinteza i ispitivanje efekta rastvarača na UV spektre 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona | sr |
dc.type | article | |
dc.rights.license | BY-NC-ND | |
dc.citation.epage | 516 | |
dc.citation.issue | 8 | |
dc.citation.other | 66(8): 507-516 | |
dc.citation.rank | M23 | |
dc.citation.spage | 507 | |
dc.citation.volume | 66 | |
dc.identifier.fulltext | http://TechnoRep.tmf.bg.ac.rs/bitstream/id/13198/0352-51390108507M.pdf | |
dc.identifier.rcub | https://hdl.handle.net/21.15107/rcub_technorep_390 | |
dc.identifier.scopus | 2-s2.0-0040488617 | |
dc.identifier.wos | 000171949000002 | |
dc.type.version | publishedVersion |