Aromaticity of H-bonded and metal complexes of guanine tautomers

Olga Stasyuk , Halina Szatyłowicz , Tadeusz Marek Krygowski


The effect of H-bonding and metal complexation (probed by HF, F−, Li+, Na+, and K+) on structural and π-electron delocalization changes in four most stable guanine tautomers and their structural subunits has been studied in the gas phase using the B3LYP/6−311++G(2d,2p) computational level. In both cases, i.e., H-bonding and metal complexation, the strongest interactions are found in bifurcated complexes of the keto guanine tautomers. Interactions in which the functional groups participate (NH2 or C=O) regularly lead to the greatest geometric and aromaticity changes. As a consequence, aromaticity of substituted six-membered rings is decisive for aromaticity of whole ring system in guanine tautomers. Aromaticity of guanine tautomers and their structural subunits changes in the same way (increase or decrease) depending on particular type of interactions.
Author Olga Stasyuk ZChF
Olga Stasyuk,,
- Department Of Physical Chemistry
, Halina Szatyłowicz ZChF
Halina Szatyłowicz,,
- Department Of Physical Chemistry
, Tadeusz Marek Krygowski
Tadeusz Marek Krygowski,,
Journal seriesStructural Chemistry, ISSN 1040-0400
Issue year2016
Publication size in sheets0.5
Keywords in EnglishGuanine; Aromaticity; HOMA index; Hydrogen bonding; Metal cation
Languageen angielski
art%3A10.1007%2Fs11224-015-0605-9.pdf 558.6 KB
Score (nominal)25
ScoreMinisterial score [Punktacja MNiSW] = 25.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) [Punktacja MNiSW (2013-2016)] = 25.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor [Impact Factor WoS]: 2016 = 1.582 (2) - 2016=1.372 (5)
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