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

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

Leonid Isaakovich Belen'kii 1
Leonid Isaakovich Belen'kii
, 
Maxim Ruslanovich Radzhabov 1, 2
Maxim Ruslanovich Radzhabov
, 
Tatyana Stepanovna Pivina 1
Tatyana Stepanovna Pivina
10.1016/j.mencom.2018.09.034
Published 2018-09-07
Communication , Volume 28, Issue 5, 548-550
2
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Belen'kii L. I., Radzhabov M. R., Pivina T. S. Quantum-chemical study of the mechanism of aminomethylation of tetrazoles according to the elimination–addition scheme without preliminary formation of N-protonated azolium salts // Mendeleev Communications. 2018. Vol. 28. No. 5. pp. 548-550.
GOST all authors (up to 50) Copy
Belen'kii L. I., Radzhabov M. R., Pivina T. S. Quantum-chemical study of the mechanism of aminomethylation of tetrazoles according to the elimination–addition scheme without preliminary formation of N-protonated azolium salts // Mendeleev Communications. 2018. Vol. 28. No. 5. pp. 548-550.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2018.09.034
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.034
TI - Quantum-chemical study of the mechanism of aminomethylation of tetrazoles according to the elimination–addition scheme without preliminary formation of N-protonated azolium salts
T2 - Mendeleev Communications
AU - Belen'kii, Leonid Isaakovich
AU - Radzhabov, Maxim Ruslanovich
AU - Pivina, Tatyana Stepanovna
PY - 2018
DA - 2018/09/07
PB - Mendeleev Communications
SP - 548-550
IS - 5
VL - 28
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2018_Belen'kii,
author = {Leonid Isaakovich Belen'kii and Maxim Ruslanovich Radzhabov and Tatyana Stepanovna Pivina},
title = {Quantum-chemical study of the mechanism of aminomethylation of tetrazoles according to the elimination–addition scheme without preliminary formation of N-protonated azolium salts},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.034},
number = {5},
pages = {548--550},
doi = {10.1016/j.mencom.2018.09.034}
}
MLA
Cite this
MLA Copy
Belen'kii, Leonid Isaakovich, et al. “Quantum-chemical study of the mechanism of aminomethylation of tetrazoles according to the elimination–addition scheme without preliminary formation of N-protonated azolium salts.” Mendeleev Communications, vol. 28, no. 5, Sep. 2018, pp. 548-550. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.034.

Abstract

Based on analysis of quantum chemical DFT/B3LYP/6-31G(d) calculations results, thermodynamic characteristics of electrophilic dimethylaminomethylation of 1H-tetrazole and 1-methyl-tetrazole 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.

References

1.
Alternative mechanisms of electrophilic substitution in azole series
Belen’kii L.I., Chuvylkin N.D.
Russian Chemical Bulletin, 2016
2.
The kinetics and mechanism of the electrophilic substitution of heteroaromatic compounds. Part XXXVIII. Hydrogen exchange of isoxazoles and isothiazoles
Clementi S., Forsythe P.P., Johnson C.D., Katritzky A.R., Terem B.
Journal of the Chemical Society Perkin Transactions 2, 1974
3.
The kinetics and machanism of the electrophilic substitution of heteroaromatic compounds. Part XXXI. The standardisation of acid catalysed hydrogen exchange rates
El-Anani A., Banger J., Bianchi G., Clementi S., Johnson C.D., Katritzky A.R.
Journal of the Chemical Society Perkin Transactions 2, 1973
4.
The kinetics and mechanism of the electrophilic substitution of heteroaromatic compounds. Part XXXIV. The hydrogen-exchange rates of methylpyrazoles
Clementi S., Forsythe P.P., Johnson C.D., Katritzky A.R.
Journal of the Chemical Society Perkin Transactions 2, 1973
5.
The standardization of aromatic and heteroaromatic nitration rates
Katritzky A.R., Terem B., Scriven E.V., Clementi S., Tarhan H.O.
Journal of the Chemical Society Perkin Transactions 2, 1975
6.
Discussion of standard nitration rates for benzenoid and heteroaromatic compounds
Katritzky A.R., Clementi S., Tarhan H.O.
Journal of the Chemical Society Perkin Transactions 2, 1975
7.
The kinetics and mechanism of the electrophilic substitution of heteroaromatic compounds. Part XLII. The nitration of thiazoles and thiazolones
Katritzky A.R., Ögretir C., Tarhan H.O., Dou H.M., Metzger J.V.
Journal of the Chemical Society Perkin Transactions 2, 1975
8.
The kinetics and mechanism of the electrophilic substitution of heteroaromatic compounds. Part XLIII. The nitration of isothiazoles
Katritzky A.R., Tarhan H.O., Terem B.
Journal of the Chemical Society Perkin Transactions 2, 1975
10.
Relationships and features of electrophilic substitution reactions in the azole series
Belen'kii L.I., Chuvylkin N.D.
Chemistry of Heterocyclic Compounds, 1997
11.
10.1016/j.mencom.2018.09.034_bib0055
Gaponik
Chemical Problems of the Development of New Materials and Technologies, 2003
17.
10.1016/j.mencom.2018.09.034_bib0085
Ostrovskii
2008
18.
Aminomethylation of 1-R-Tetrazoles
Karavai V.P., Gaponik P.N.
Chemistry of Heterocyclic Compounds, 1991
19.
10.1016/j.mencom.2018.09.034_bib0095
Butler
1996
20.
10.1016/j.mencom.2018.09.034_bib0100
Frisch
Gaussian 09. Revision D. 01, 2013
22.
10.1016/j.mencom.2018.09.034_bib0110
Belen’kii
Russ. Chem. Bull., Int. Ed., 2016
23.
10.1016/j.mencom.2018.09.034_bib0115
Terentiev
1957
24.
10.1016/j.mencom.2018.09.034_bib0120
Furin
Sovremennye metody ftorirovaniya organicheskih soedinenii (Modern Methods of Fluorination of Organic Compounds), 2000
25.
Recent Advances in Bromination of Aromatic and Heteroaromatic Compounds
Voskressensky L., Golantsov N., Maharramov A.
Synthesis, 2016
27.
10.1016/j.mencom.2018.09.034_bib0135
Schoeller
Ber., 1919
28.
10.1016/j.mencom.2018.09.034_bib0140
Makarova
Metody elementoorganicheskoi khimii. Rtut (Methods of Organoelement Chemistry. Mercury), 1965
29.
Ananikov V.P., Galkin K.I., Egorov M.P., Sakharov A.M., Zlotin S.G., Redina E.A., Isaeva V.I., Kustov L.M., Gening M.L., Nifantiev N.E.
Mendeleev Communications, 2016