The azido-tetrazole and diazo-1,2,3-triazole tautomerism in six-membered heteroaromatic rings and their relationships with aromaticity: Azines and perimidine

被引：55

作者：

Alkorta, Ibon ^{[1
]}

Blanco, Fernando ^{[1
]}

Elguero, Jose ^{[1
]}

Claramunt, Rosa M. ^{[2
]}

机构：

[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain

[2] Univ Nacl Educ Distancia, Fac Ciencias, Dept Quim Organ & Bioorgan, E-28040 Madrid, Spain

来源：

TETRAHEDRON | 2010年 / 66卷 / 15期

关键词：

Azido; Tetrazole; Diazo; 1,2,3-Triazole; Azines; Perimidine; DFT calculations; INDEPENDENT CHEMICAL-SHIFTS; MOLECULAR-ORBITAL METHODS; HETEROCYCLIC-ANALOGS; ENERGETIC PROPERTIES; 5-MEMBERED RINGS; EQUILIBRIUM; DENSITY; DERIVATIVES; ISOMERIZATION; SPECTROSCOPY;

D O I：

10.1016/j.tet.2010.02.035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The properties of 28 molecules together with 12 transition states belonging to the series of azido-azines, tetrazolo-azines, diazo-azines, and 1,2,3-triazolo-azines have been studied at the B3LYP/6-31G(d), B3LYP/6-311++G(d,p) and, for 26 cases, at the G3B3 level. Energies. NICS and bond critical points were used to discuss the ring-chain tautomerism of these compounds in relation with the aromaticity of the azines (pyridine, pyrimidine, quinazoline, 1,3-diazapyrene, and perimidine) and the azoles (tetrazoles and 1,2,3-triazoles). (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2863 / 2868

页数：6

共 89 条

[1] Azido-tetrazole equilibrium in 2-azidothiazole system. Molecular orbital calculations [J].