Cover Picture: The Role of Aromaticity, Hybridization, Electrostatics, and Covalency in Resonance‐Assisted Hydrogen Bonds of Adenine–Thymine (AT) Base Pairs and Their Mimics (ChemistryOpen 3/2015)

ChemistryOpen

L. Guillaumes¹  Dr. S. Simon¹ 

[1] Institut de Química Computacional i Catàlisi, Departament de Química, Universitat de Girona, Girona, Spain)

关键词: aromaticity;    density functional calculations;    DNA base pairs;    molecular orbital (MO) theory;    nucleotides;    resonance-assisted hydrogen bonding;   

DOI  :  10.1002/open.201580301

来源: Wiley

【 摘 要 】

Abstract

The cover picture shows hydrogen bonds in the adenine–thymine (AT) Watson–Crick base pair. An essential part of these H-bonds is their covalent component that arises from donor–acceptor interactions between the N or O lone pairs and the N–H antibonding σ* acceptor orbital. This charge-transfer interaction is represented by the green figures walking over the pedestrian crossing, connecting the two bases. We reveal that this covalent component is the reason why H-bonds between DNA bases and/or unsaturated model bases are significantly stronger than those between analogous saturated bases. This contrasts sharply with the classical picture of predominantly electrostatic H-bonds which is not only incomplete in terms of a proper bonding mechanism, but also fails to explain the trend in stability. For more details, see the Full Paper on p. 318 ff.

【 授权许可】

Unknown   
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim