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Sinteza i ispitivanje efekta rastvarača na UV spektre 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona

dc.creatorMijin, Dušan
dc.creatorUšćumlić, Gordana
dc.creatorValentić, Nataša
dc.date.accessioned2021-03-10T09:57:45Z
dc.date.available2021-03-10T09:57:45Z
dc.date.issued2001
dc.identifier.issn0352-5139
dc.identifier.urihttp://TechnoRep.tmf.bg.ac.rs/handle/123456789/390
dc.description.abstractA 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.abstractU 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.publisherSerbian Chemical Society, Belgrade
dc.rightsopenAccess
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/
dc.sourceJournal of the Serbian Chemical Society
dc.subjectalkylationen
dc.subjectethyl acetoacetateen
dc.subjectalkyl ethyl acetoacetates synthesisen
dc.subject5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridonesen
dc.subjectspectroscopyen
dc.subjectcyclizationen
dc.subjectultraviolet absorption spectraen
dc.subjectsolvent effectsen
dc.subjectlinear solvation energy relationshipsen
dc.titleSynthesis and investigation of solvent effects on the ultraviolet absorption spectra of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridonesen
dc.titleSinteza i ispitivanje efekta rastvarača na UV spektre 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridonasr
dc.typearticle
dc.rights.licenseBY-NC-ND
dc.citation.epage516
dc.citation.issue8
dc.citation.other66(8): 507-516
dc.citation.rankM23
dc.citation.spage507
dc.citation.volume66
dc.identifier.fulltexthttp://TechnoRep.tmf.bg.ac.rs/bitstream/id/13198/0352-51390108507M.pdf
dc.identifier.rcubhttps://hdl.handle.net/21.15107/rcub_technorep_390
dc.identifier.scopus2-s2.0-0040488617
dc.identifier.wos000171949000002
dc.type.versionpublishedVersion


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