Quantum chemical studies of azoles 5*. Electrophilic substitution in tetrazole and 1,2,4-triazole: the influence of basis set on calculated thermodynamic parameters of the elimination-addition mechanism without preliminary formation of N-protonated azolium salts

被引：11

作者：

Belen'kii, L. I. ^{[1
]}

Subbotin, A. N. ^{[1
]}

Chuvylkin, N. D. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2015年 / 64卷 / 11期

基金：

俄罗斯科学基金会;

关键词：

azoles; electrophilic substitution; 1H-tetrazole; 1H-1,2,4-triazole; quantum chemical calculations; DFT/B3LYP/6-31G(2df; p); method; NEUTRAL MOLECULES;

D O I：

10.1007/s11172-015-1198-6

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Thermodynamic parameters of electrophilic substitution reactions of 1H-tetrazole and 1H-1,2,4-triazole proceeding by the addition-elimination and elimination-addition mechanisms were calculated by the DFT/B3LYP/6-31G(2df,p) method using proton as model electrophile and compared. The results obtained substantiate that the elimination-addition mechanism may not involve preliminary formation of N-protonated azolium salts, as was shown earlier in our DFT/B3LYP/6-31G(d,p) calculations.

引用

页码：2610 / 2614

页数：5