Home / Publications / A DFT study on the regioselectivity and molecular mechanism of nitroethene [2 + 3] cycloaddition to (Z)-C,N-diphenylnitrone and C,C,N-triphenylnitrone

A DFT study on the regioselectivity and molecular mechanism of nitroethene [2 + 3] cycloaddition to (Z)-C,N-diphenylnitrone and C,C,N-triphenylnitrone

Radomir Jasiński 1
Radomir Jasiński
, 
Oscar Iosifovich Koifman 2
Oscar Iosifovich Koifman
, 
Andrzej Barański 1
Andrzej Barański
10.1016/j.mencom.2011.09.010
Published 2011-09-14
Communication , Volume 21, Issue 5, 262-263
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Jasiński R., Koifman O. I., Barański A. A DFT study on the regioselectivity and molecular mechanism of nitroethene [2 + 3] cycloaddition to (Z)-C,N-diphenylnitrone and C,C,N-triphenylnitrone // Mendeleev Communications. 2011. Vol. 21. No. 5. pp. 262-263.
GOST all authors (up to 50) Copy
Jasiński R., Koifman O. I., Barański A. A DFT study on the regioselectivity and molecular mechanism of nitroethene [2 + 3] cycloaddition to (Z)-C,N-diphenylnitrone and C,C,N-triphenylnitrone // Mendeleev Communications. 2011. Vol. 21. No. 5. pp. 262-263.
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TY - JOUR
DO - 10.1016/j.mencom.2011.09.010
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.09.010
TI - A DFT study on the regioselectivity and molecular mechanism of nitroethene [2 + 3] cycloaddition to (Z)-C,N-diphenylnitrone and C,C,N-triphenylnitrone
T2 - Mendeleev Communications
AU - Jasiński, Radomir
AU - Koifman, Oscar Iosifovich
AU - Barański, Andrzej
PY - 2011
DA - 2011/09/14
PB - Mendeleev Communications
SP - 262-263
IS - 5
VL - 21
ER -
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@article{2011_Jasiński,
author = {Radomir Jasiński and Oscar Iosifovich Koifman and Andrzej Barański},
title = {A DFT study on the regioselectivity and molecular mechanism of nitroethene [2 + 3] cycloaddition to (Z)-C,N-diphenylnitrone and C,C,N-triphenylnitrone},
journal = {Mendeleev Communications},
year = {2011},
volume = {21},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.09.010},
number = {5},
pages = {262--263},
doi = {10.1016/j.mencom.2011.09.010}
}
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Jasiński, Radomir, et al. “A DFT study on the regioselectivity and molecular mechanism of nitroethene [2 + 3] cycloaddition to (Z)-C,N-diphenylnitrone and C,C,N-triphenylnitrone.” Mendeleev Communications, vol. 21, no. 5, Sep. 2011, pp. 262-263. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.09.010.

Abstract

Global and local reactivity indexes indicate a polar character of the [2 + 3] cycloaddition of nitroethene to (Z)-C,N-diphenylnitrone and C,C,N-triphenylnitrone. The regioselectivity of the reactions is determined by the attack of an oxygen-centred nucleophilic site of the nitrone on the b-carbon atom in nitroethene, which is confirmed by B3LYP/6-31G(d) simulations of the reaction pathways. Although the transition complexes are considerably asymmetric and polar, the reactions proceed via a concerted mechanism.

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