NDLI: Nucleophilic properties of purine bases: inherent reactivity versus reaction conditions

Content Provider	Springer Nature Link
Author	Stachowicz Kuśnierz, Anna Korchowiec, Jacek
Copyright Year	2015
Abstract	In the present study, nucleophilic properties of adenine and guanine are examined by means of density functional theory. H$^{+}$ is used as a model electrophile. Two modes of H$^{+}$ attack on the bases are considered: on the neutral molecule and on the anion. Solvent effects are modeled by means of polarizable continuum model. Regioselectivity of attack is studied by analyzing two contributions. The first one is the energetic ordering of the tautomers. The second is the relative inherent reactivity of nucleophilic sites in the bases. Atomic softnesses calculated by means of charge sensitivity analysis are employed for this purpose. The most reactive sites in various tautomers are identified on the ground of Li–Evans model. For adenine, it is demonstrated that both in basic and in neutral pH N7 atom possesses the most nucleophilic character. In polar solvents, N7 substitution is also most favored energetically. In basic pH and nonpolar solvents as well as in the gas phase, N9 substitution is slightly more probable. For guanine, a mixture of N7- and N9-substituted products can be expected in basic pH. In neutral pH, inherent reactivity and energy trends are opposite to each other; therefore, the substitution does not occur. Experimentally observed products of reactions with various electrophiles and in various conditions confirm the results obtained in this study.
Starting Page	543
Ending Page	555
Page Count	13
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	27
Issue Number	2
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2015-03-15
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Purine bases Electrophilic attack Solvent effects Reactivity indices Fukui function Computer Applications in Chemistry Physical Chemistry Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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