Quantum-chemical study of the mechanism of aminomethylation of tetrazoles according to the elimination-addition scheme without preliminary formation of N-protonated azolium salts

被引：1

作者：

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

Radzhabov, Maxim R. ^{[1
]}

Pivina, Tatyana S. ^{[1
]}

机构：

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

来源：

MENDELEEV COMMUNICATIONS | 2018年 / 28卷 / 05期

基金：

俄罗斯科学基金会;

关键词：

ELECTROPHILIC SUBSTITUTION; 1,2,4-TRIAZOLE; MERCURISATION;

D O I：

10.1016/j.mencom.2018.09.034

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Based on analysis of quantum chemical DFT/B3LYP/6-31G(d) calculations results, thermodynamic characteristics of electro-philic dimethylaminomethylation of 1H-tetrazole and 1-methyltetrazole according to addition elimination and elimination-addition schemes were correlated. The possibility of the dimethylaminomethylation without the preliminary formation of N-protonated azolium salts was demonstrated.

引用

页码：548 / 550

页数：3

共 14 条

[1] Quantum chemical studies of azoles 9. Tetrazole halogenation according to the elimination-addition scheme without preliminary formation of N-protonated azolium salts
Belen'kii, L. I.
Subbotin, A. N.
Chuvylkin, N. D.
RUSSIAN CHEMICAL BULLETIN, 2016, 65 (11) : 2578 - 2582
[2] Quantum chemical studies of azoles 9. Tetrazole halogenation according to the elimination—addition scheme without preliminary formation of N-protonated azolium salts
L. I. Belen’kii
A. N. Subbotin
N. D. Chuvylkin
Russian Chemical Bulletin, 2016, 65 : 2578 - 2582
[3] Quantum chemical studies of azoles 6. The effect of specific solvation on the calculated thermodynamic parameters of electrophilic substitution in tetrazole according to the elimination-addition scheme without preliminary formation of N-protonated azolium salts
Chuvylkin, N. D.
Subbotin, A. N.
Belen, L. I.
RUSSIAN CHEMICAL BULLETIN, 2016, 65 (04) : 939 - 943
[4] Quantum chemical studies of azoles 8.* Effect of N(2)-methyl substituent on the calculated thermodynamic parameters of electrophilic substitution in tetrazole according to the elimination-addition scheme without preceding formation of N-protonated azolium salts
Belen'kii, L. I.
Subbotin, A. N.
Chuvylkin, N. D.
RUSSIAN CHEMICAL BULLETIN, 2016, 65 (07) : 1722 - 1726
[5] Quantum chemical studies of azoles11.* Transition states in the routes of electrophilic substitution in 2H-tetrazole via the elimination-addition mechanism without preliminary formation of N-protonated azolium salts
Chuvylkin, N. D.
Subbotin, A. N.
Belov, S. A.
Belen'kii, L. I.
RUSSIAN CHEMICAL BULLETIN, 2017, 66 (06) : 941 - 945
[6] Quantum chemical studies of azoles 10. Transition states in the routes of electrophilic substitution in 1H-tetrazole via the elimination-addition mechanism without preliminary formation of N-protonated azolium salts
Chuvylkin, N. D.
Subbotin, A. N.
Belen'kii, L. I.
RUSSIAN CHEMICAL BULLETIN, 2017, 66 (05) : 808 - 812
[7] Quantum chemical studies of azoles 6. The effect of specific solvation on the calculated thermodynamic parameters of electrophilic substitution in tetrazole according to the elimination—addition scheme without preliminary formation of N-protonated azolium salts
N. D. Chuvylkin
A. N. Subbotin
L. I. Belen´kii
Russian Chemical Bulletin, 2016, 65 : 939 - 943
[8] 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
Belen'kii, L. I.
Subbotin, A. N.
Chuvylkin, N. D.
RUSSIAN CHEMICAL BULLETIN, 2015, 64 (11) : 2610 - 2614
[9] Quantum chemical studies of azoles 8. Effect of N(2)-methyl substituent on the calculated thermodynamic parameters of electrophilic substitution in tetrazole according to the elimination–addition scheme without preceding formation of N-protonated azolium salts
L. I. Belen’kii
A. N. Subbotin
N. D. Chuvylkin
Russian Chemical Bulletin, 2016, 65 : 1722 - 1726
[10] Quantum chemical studies of azoles 7.* N-Alkyl substituent effect on calculated thermodynamic parameters of the electrophilic substitution mechanism in 1H-tetrazole via elimination-addition scheme without preceding formation of N-protonated azolium salts
Chuvylkin, N. D.
Subbotin, A. N.
Belen'kii, L. I.
RUSSIAN CHEMICAL BULLETIN, 2016, 65 (07) : 1716 - 1721

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