An ab initio study on nucleic acid bases aromaticities

被引：79

作者：

Cysewski, P ^{[1
]}

机构：

[1] Nicholas Copernicus Univ, Coll Med, Dept Phys Chem, PL-85950 Bydgoszcz, Poland

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 2005年 / 714卷 / 01期

关键词：

aromaticity; HOMA; NICS; adenine; guanine; cytosine; thymine; uracil; DNA bases; ab initio; DFT;

D O I：

10.1016/j.theochem.2004.10.030

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Aromatic character of nucleic acid bases was characterized by means of magnetic and geometric properties. Optimized geometries at DFr/6-311 + G** level were used for calculation of nucleus independent chemical shift (NICS) and harmonic oscillator model of aromaticity (HOMA) values. Aromaticities of both pyrimidine and imidazole rings were analyzed. Solvent impact on HOMA values was estimated. Predictions of both methods are in qualitative agreement and suggest more aromatic character of purities rather than pyrimidines. Aromaticity decreases in the following sequence: adenine > guanine > cytosine > thymine = uracil. Significant impact of protonation on the aromatic character was noticed. Protonation of adenine reduced its aromatic character of both pyrimidine and imidazole rings. However, protonation of guanine and all pyrimidines leads to increase of aromaticity compared to neutral species. (C) 2004 Elsevier B.V. All rights reserved.

引用

页码：29 / 34

页数：6

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