Brønsted acidic ionic liquids and their zwitterions: synthesis, characterization and pKa determination

Chemistry : a European Journal
Zhaofu FeiPaul J Dyson

Abstract

Imidazolium chlorides with one or two carboxylic acid substituent groups, 1-methyl-3-alkylcarboxylic acid imidazolium chloride, [Me[(CH2)nCOOH]im]Cl (n=1, 3), and 1,3-dialkylcarboxylic acid imidazolium chloride, [[(CH2)nCOOH]2im]Cl (n=1, 3), have been synthesized via their corresponding acid esters. Deprotonation of the carboxylic acid functionalized imidazolium chlorides with triethylamine affords the corresponding zwitterions [Me[(CH2)nCOO]im] (n=1, 3) and [[(CH2)nCOOH][(CH2)nCOO]im] (n=1, 3). Subsequent reaction of the zwitterions with strong acids gives the new imidazolium salts [Me[(CH2)nCOOH]im]X (n=1, 3; X=BF4, CF3SO3) and [[(CH2)nCOOH]2im]X (n=1, 3; X=BF4, CF3SO3), which exhibit melting points as low as -61 degrees C. The solid-state structures of two of the carboxylic acid functionalized imidazolium salts have been determined by single-crystal X-ray diffraction analysis. Extensive hydrogen bonding is present between the chloride and the imidazolium, with eight Cl.H interactions below 3 A. The pK(a) values of all the salts, determined by potentiometric titration, lie between 1.33 and 4.59 at 25 degrees C.

Citations

May 28, 1976·Biochimica Et Biophysica Acta·T FrickJ M Wood
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Jinling MiaoYong Nie
May 6, 2015·Chemical Communications : Chem Comm·David DupontKoen Binnemans
Mar 8, 2016·Chemical Communications : Chem Comm·David DupontKoen Binnemans
Nov 2, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sang Eun SimSangho Koo
Aug 8, 2009·European Journal of Mass Spectrometry·Ilva NakurteSvetlana Dubrovina
Nov 9, 2007·Physical Chemistry Chemical Physics : PCCP·Kaoru NobuokaYuichi Ishikawa
Dec 2, 2008·Chemistry : a European Journal·Qinghua ZhangYouquan Deng
Oct 2, 2009·ChemSusChem·Elizeo LissnerJairton Dupont
Oct 17, 2009·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Qing-Tao WangJing-Cheng Hao
Feb 4, 2010·Physical Chemistry Chemical Physics : PCCP·Geoffrey L BurrellNoel F Dunlop
Mar 15, 2006·Chemistry : a European Journal·Zhaofu FeiPaul J Dyson
Mar 16, 2019·Chemistry : a European Journal·Palraj KasinathanAntony E Fernandes
May 30, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Elena BorregoAgustín Galindo
May 28, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Xuan WangEn-Qing Gao
Sep 20, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Lei ZhangGuo-Hong Tao
Sep 10, 2015·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Jingjing LiChengbu Liu
Sep 15, 2020·ChemSusChem·Francisco Del MonteM Luisa Ferrer
Mar 15, 2012·Physical Chemistry Chemical Physics : PCCP·Jing LiThomas Drewello
Sep 3, 2013·Chemical Communications : Chem Comm·Denis ProdiusAnnie K Powell
Oct 8, 2013·Acta Crystallographica. Section C, Crystal Structure Communications·Heng ZhangXiaopeng Xuan
Aug 7, 2007·The Journal of Physical Chemistry. B·Zhaofu FeiPaul J Dyson
Jan 2, 2009·Inorganic Chemistry·Lijun HanXingmei Lu
Apr 14, 2009·Chemical Reviews·Joseph C Y LinIvan J B Lin
Dec 22, 2007·Chemical Reviews·Tamar L Greaves, Calum J Drummond
Nov 23, 2010·The Journal of Physical Chemistry. B·Masahiro Yoshizawa-FujitaHiroyuki Ohno
Jan 18, 2013·The Journal of Physical Chemistry. B·Renato ContrerasAndrea Cerda-Monje
May 28, 2011·The Journal of Physical Chemistry. a·Afshan Mohajeri, Abolfazl Ashrafi
Mar 13, 2014·The Journal of Physical Chemistry. B·Andrea Cerda-MonjeRenato Contreras

❮ Previous
Next ❯

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.