Tautomerism and Structure of Azoles: Nuclear Magnetic Resonance Spectroscopy

被引：42

作者：

Larina, Lyudmila I. ^{[1
]}

机构：

[1] Russian Acad Sci, Siberian Branch, Irkutsk, Russia

来源：

ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 124 | 2018年 / 124卷

关键词：

Azoles; Benzazoles; Dynamic NMR; Imidazoles; Multinuclear NMR spectroscopy; Pyrazoles; Structure and tautomerism; Terazoles; Triazoles; N-15; NMR-SPECTROSCOPY; ONE-POT SYNTHESIS; C-13; NMR; SOLID-STATE; X-RAY; MOLECULAR-STRUCTURE; PROTON-TRANSFER; GAS-PHASE; AB-INITIO; CHEMICAL-SHIFTS;

D O I：

10.1016/bs.aihch.2017.06.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review provides comprehensive data (from the author's work and the literature) on tautomerism of pyrazoles, imidazoles, 1,2,3- and 1,2,4-triazoles, tetrazoles, benzimidazoles, benzimidazolones, benzotriazoles, and related compounds by multinuclear H-1, C-13, N-15 nuclear magnetic resonance (NMR) spectroscopy. Emphasis is given to studies of azoles by multinuclear dynamic NMR spectroscopy because prototropic transformations of almost all azoles in solution proceed so quickly. Quantum-chemical investigations of tautomeric azoles are covered in detail. Critical analysis of literature data on the tautomerism of azoles is presented. Theoretical studies of structure and reactivity of azoles are most intriguing because correct interpretation of their chemical behavior and biological activity depends on an understanding the factors determining relative stability of their tautomers. N-15 NMR spectroscopy is the most reliable and fast technique for structural and tautomeric determination of nitrogen-containing heteroaromatic compounds.

引用

页码：233 / 321

页数：89

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