On the aromatic character of the heterocyclic bases of DNA and RNA

被引：65
作者：
Cyranski, MK
Gilski, M
Jaskólski, M
Krygowski, TM
机构：
[1] Univ Warsaw, Dept Chem, PL-02093 Warsaw, Poland
[2] Adam Mickiewicz Univ Poznan, Fac Chem, Dept Crystallog, Poznan, Poland
[3] Polish Acad Sci, Inst Bioorgan Chem, Ctr Biocrystallograph Res, Poznan, Poland
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 22期
关键词：
D O I：
10.1021/jo034760e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Studies based on ab initio optimized geometries (at B3LYP/6-311+G** and MP2/6-311+G** levels) and on experimental structures retrieved from the Cambridge Structural Database (CSD) reveal that the nucleobases constituting DNA and RNA differ significantly in their aromatic character, as shown by the geometry-based index of aromaticity HOMA that ranges from 0.466 for thymine to 0.917 for adenine, based on B3LYP/6-311+G** calculations, and 0.495-0.926, respectively, if based on the MP2/6-311+G** level. Aromaticity of the bases decreases markedly with an increase of the number of double-bond C=X (X = N, 0) substituents at the rings. H-bonds involving C=O groups in Watson-Crick pairs cause an increase of the aromatic character of the rings.
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页码：8607 / 8613
页数：7
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