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

被引：8

作者：

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

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

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

机构：

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

来源：

RUSSIAN CHEMICAL BULLETIN | 2016年 / 65卷 / 04期

基金：

俄罗斯科学基金会;

关键词：

azoles; electrophilic substitution; 1H-tetrazole; quantum chemical calculations; DFT/B3LYP/6-31G(d); HYDROXIDE ION; NEUTRAL MOLECULES; CH ACIDITY;

D O I：

10.1007/s11172-016-1395-y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Quantum chemical calculations (DFT/B3LYP/6-31G(d)) considering specific solvation effects were used to compare the thermodynamic parameters of electrophilic substitution reactions (with the hydroxonium ion as a model electrophile) in 1H-tetrazole according to the addition-elimination and elimination-addition schemes. The latter scheme can proceed without preliminary formation of N-protonated azolium salts, as demonstrated earlier by the DFT/ B3LYP/6-31G(d,p) and DFT/B3LYP/6-31G(2df,p) calculations considering the solvation effects in aqueous solution in terms of the polarizable continuum model (PCM) with a proton as a model electrophile.

引用

页码：939 / 943

页数：5

共 16 条

[1] 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
[2] 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
[3] 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
[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
L. I. Belen’kii
A. N. Subbotin
N. D. Chuvylkin
Russian Chemical Bulletin, 2016, 65 : 1722 - 1726
[5] 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
[6] 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
[7] 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
[8] 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
[9] 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
[10] Quantum-chemical study of the mechanism of aminomethylation of tetrazoles according to the elimination-addition scheme without preliminary formation of N-protonated azolium salts
Belen'kii, Leonid I.
Radzhabov, Maxim R.
Pivina, Tatyana S.
MENDELEEV COMMUNICATIONS, 2018, 28 (05) : 548 - 550

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