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Substituent effects on the stability of the four most stable tautomers of adenine and purine

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cris.lastimport.scopus2024-02-12T20:11:17Z
dc.abstract.en<p>Substituent effects at the C2-, C8- and N-positions of adenine and purine in their four the most stable tautomers are studied by means of B97D3/aug-cc-pvdz computation applying substituents of varying electronic properties: NO<sub>2</sub>, CN, CHO, Cl, F, H, Me, OMe, OH and NH<sub>2</sub>. The substituent effect is characterized by the substituent effect stabilization energy (SESE) and substituent Hammett constant σ. For adenine, SESE is obtained with purine as the reference system. Additionally, for both adenine and purine, SESE characteristics are estimated with benzene, imidazole and amino-pyrimidine as reference systems, when possible, taking into account substitution in topologically equivalent positions. The role of a C6-NH<sub>2</sub> group in adenine in modifying the substitution effect is observed and discussed. Additionally, the proximity effect for some asymmetric substituents (e.g. CHO, OMe) is recognized and meticulously analyzed.</p>
dc.affiliationUniwersytet Warszawski
dc.contributor.authorJezuita, Anna Ewa
dc.contributor.authorMarek, Paulina H.
dc.contributor.authorKrygowski, Tadeusz
dc.contributor.authorSzatyłowicz, Halina
dc.date.accessioned2024-01-26T09:21:06Z
dc.date.available2024-01-26T09:21:06Z
dc.date.copyright2019-10-02
dc.date.issued2019
dc.description.accesstimeAT_PUBLICATION
dc.description.financeNie dotyczy
dc.description.number54
dc.description.versionFINAL_PUBLISHED
dc.description.volume9
dc.identifier.doi10.1039/C9RA04615A
dc.identifier.issn2046-2069
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/121069
dc.identifier.weblinkhttps://pubs.rsc.org/en/content/articlehtml/2019/ra/c9ra04615a
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofRSC Advances
dc.relation.pages31343-31356
dc.rightsCC-BY
dc.sciencecloudnosend
dc.titleSubstituent effects on the stability of the four most stable tautomers of adenine and purine
dc.typeJournalArticle
dspace.entity.typePublication