Does the Intramolecular Hydrogen Bond Affect the Spectroscopic Properties of Bicyclic Diazole Heterocycles?

被引：5

作者：

Misiak, Pawel ^{[1
]}

Dubis, Alina T. ^{[1
]}

Lapinski, Andrzej ^{[2
]}

机构：

[1] Univ Bialystok, Inst Chem, Ciolkowskiego 1K, PL-15245 Bialystok, Poland

[2] Polish Acad Sci, Inst Mol Phys, Smoluchowskiego 17, PL-60179 Poznan, Poland

来源：

JOURNAL OF SPECTROSCOPY | 2018年 / 2018卷

关键词：

AB-INITIO; AROMATIC CHARACTER; BASIS-SETS; PERAMINE; ATOMS; RING; VAN; STABILIZATION; FORCE; INDEX;

D O I：

10.1155/2018/1048157

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

The formation of an intramolecular hydrogen bond in pyrrolo[1,2-a]pyrazin-1(2H)-one bicyclic diazoles was analyzed, and the influence of N-substitution on HB formation is discussed in this study. B3LYP/aug-cc-pVDZ calculations were performed for the diazole, and the quantum theory of atoms in molecules (QTAIM) approach as well as the natural bond orbital (NBO) method was applied to analyze the strength of this interaction. It was found that the intramolecular hydrogen bond that closes an extra ring between the C=O proton acceptor group and the CH proton donor, that is, C=O center dot center dot center dot H-C, influences the spectroscopic properties of pyrrolopyrazine bicyclic diazoles, particularly the carbonyl frequencies. The influence of N-substitution on the aromaticity of heterocyclic rings is also discussed in this report.

引用

页数：15

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