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.
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页码：233 / 321
页数：89
相关论文
共 543 条
[81]  
Butler R N., 1996, Comprehensive Heterocyclic Chemistry II, V4, P621, DOI DOI 10.1016/B978-008096518-5.00095-2
[82]   A STUDY OF ANNULAR TAUTOMERISM, INTERANNULAR CONJUGATION, AND METHYLATION REACTIONS OF ORTHO-SUBSTITUTED-5-ARYLTETRAZOLES USING C-13 AND H-1-NMR SPECTROSCOPY [J].
BUTLER, RN ;
GARVIN, VC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (02) :390-393
[83]   Tautomerism of aza cycles:: II.: Synthesis and structure of 5-substituted 3-(2-hydroxyethylsulfanyl)-1H-1,2,4-triazoles and their salts.: Preference of the 1H,4H-1,2,4-triazolium tautomers [J].
Buzykin, B. I. ;
Mronova, E. V. ;
Nabiullin, V. N. ;
Azancheev, N. M. ;
Awakumova, L. V. ;
Rizvanov, I. Kh. ;
Gubaiduffin, A. T. ;
Litvinov, I. A. ;
Syakaev, V. V. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (03) :461-479
[84]   Tautomerism of azacycles:: III.: Molecular and crystal structures of 3H- and 2-phenyl-1H,4H-4,5-dihydro-1,2,4-triazole-5-thiones [J].
Buzykin, B. I. ;
Mironova, E. V. ;
Gubaidullin, A. T. ;
Litvinov, I. A. ;
Nabiullin, V. N. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (04) :634-648
[85]   Tautomerism of aza cycles:: I.: Structure of 3(5)-butylsulfanyl-5(3)-methyl(phenyl)-1H-1,2,4-triazole tautomers in Crystal.: Preference of the 3-RA-5-RD-1H-tautomer of 3(5)-mono- and 3,5-disubstituted 1,2,4-triazoles [J].
Buzykin, B. I. ;
Mironova, E. V. ;
Nabiullin, V. N. ;
Gubaidullin, A. T. ;
Litvinov, I. A. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2006, 76 (09) :1471-1486
[86]  
CANADA J, 1985, HETEROCYCLES, V23, P2225
[87]   TAUTOMERIC EQUILIBRIA OF 3-HYDROXYPYRAZOLE IN THE GAS-PHASE AND IN SOLUTION - A THEORETICAL-STUDY COMBINING AB-INITIO QUANTUM-MECHANICS AND MONTE-CARLO SIMULATION METHODS [J].
CAO, M ;
TEPPEN, BJ ;
MILLER, DM ;
PRANATA, J ;
SCHAFER, L .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (44) :11353-11361
[88]   ARGENTOTROPISM IN (PENTAMETHYLCYCLOPENTADIENYL)IRIDIUM COMPLEXES WITH PYRAZOLE LIGANDS - MULTINUCLEAR DNMR EXPERIMENTS [J].
CARMONA, D ;
ORO, LA ;
LAMATA, MP ;
JIMENO, ML ;
ELGUERO, J ;
BELGUISE, A ;
LUX, P .
INORGANIC CHEMISTRY, 1994, 33 (10) :2196-2203
[89]   STRUCTURE OF BENZOTRIAZOLE IN THE GAS-PHASE - A UV EXPERIMENTAL-STUDY [J].
CATALAN, J ;
PEREZ, P ;
ELGUERO, J .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5276-5277
[90]  
CATALAN J, 1986, B SOC CHIM FR, P429
45678910111213