Organic and Biomolecular Chemistry p. 3170 - 3177 (2016)
Update date:2022-08-11
Topics:
Crosio, Matías A.
Correa, N. Mariano
Silber, Juana J.
Falcone, R. Darío
In this work, we have explored how the confinement of the protic ionic liquid (IL) ethylammonium nitrate (EAN) inside toluene/benzyl-n-hexadecyldimethylammonium chloride (BHDC) reverse micelles (RMs) affects the Cl- nucleophilicity on the bimolecular nucleophilic substitution (SN2) reaction between this anion and dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate. To the best of our knowledge this is the first report where toluene/BHDC RMs use EAN as a polar component and it is used as a nanoreactor for carrying out kinetic experiments. Dynamic light scattering results reveal the formation of RMs containing the protic IL. The kinetic results show that upon confinement, EAN becomes a suitable solvent for the SN2 reaction while in homogeneous media it is a bad option. Entrapped in BHDC RMs, due to the strong hydrogen bond interactions, EAN behaves as an aprotic-like IL which cannot deactivate the nucleophilic power of Cl- and yet increases the substrate solubility. These facts show the versatility of this kind of organized system to alter the polar solvent entrapped and its influence on the reaction rate when it is used as a nanoreactor.
View MoreContact:+49-4101-3053-0
Address:Waldhofstrasse 14 ,25474 Ellerbek Germany
ShangHai Original Economy-Trade Develop Co.,Ltd.,
Contact:86-21-68552131
Address:shanghai
Wuxi Forest Biological Co.,Ltd
Contact:+86-510-81602300
Address:Room 317,Building D, No.159 middle Chengjiang Road,Jiangyin Wuxi city.
Hangzhou Taiyan Trading Co., Ltd
Contact:+86-13777583958
Address:NO.63, Xingyi Street, Xihu District, Hangzhou, Zhejiang, China
Contact:0086-22-2822 1962 / 2822 1963
Address:B-808, No. 1, North-South Street, Hexi District,
Doi:10.1016/j.bioorg.2020.104584
(2021)Doi:10.1002/(sici)1099-0690(199902)1999:2<447::aid-ejoc447>3.0.co;2-r
(1999)Doi:10.1016/j.tet.2016.06.074
(2016)Doi:10.1002/chem.202004008
(2021)Doi:10.1021/jo00913a026
(1975)Doi:10.1016/j.bcp.2007.12.017
(2008)