144177-48-0Relevant articles and documents
Influence of the alkyl side chain length on the thermophysical properties of chiral ionic liquids with a (1R,2S,5R)-(–)-menthol substituent and data analysis by means of mathematical gnostics
Andresová, Adéla,Bendová, Magdalena,Schwarz, Jaroslav,Wagner, Zdeněk,Feder-Kubis, Joanna
, p. 336 - 348 (2017)
A comprehensive physico-chemical characterization of the chiral ionic liquids of a 3-alkyl-1-[(1R,2S,5R)-(–)-menthoxymethyl]imidazolium bis(trifluoromethylsulfonyl)imides homologous series with a linear alkyl substituent ranging from the methyl up to the
Synthesis and spectroscopic properties of symmetrical ionic liquids based on (?)-menthol
Feder-Kubis, Joanna
, p. 63 - 70 (2017)
Several symmetrical imidazolium salts were obtained from the natural chiral pool of (1R,2S,5R)-(?)-menthol. First 1,3-bis[(1R,2S,5R)-(?)-menthoxymethyl]imidazolium chloride, which is a prototype for ionic liquids, was prepared with the use of two different methods. Furthermore, metathesis of this symmetrical imidazolium chloride with various salts was carried out. The ion exchange reaction goes smoothly, with the satisfactory yield of 97.5 to 99.5%. Obtained 1,3-bis[(1R,2S,5R)-(?)-menthoxymethyl]imidazolium salts are stable in the air, in contact with water and in commonly used organic solvents. Moreover they are non-volatile and non-flammable. Discussed symmetrical salts belong to chiral ionic liquids (CILs) where the chirality resided in the cation and is associated with the presence of optically active (1R,2S,5R)-(?)-menthol. The diastereotopic protons in the 1H NMR were thoroughly described. Moreover, the 1H NMR and 13C NMR spectra indicated notable differences in the chemical shifts depending on the anion used. Comparing the differences between values of the chemical shifts, the anions were ordered according to their increasing shielding capacities. The changing of the electron density surrounding the imidazolium ring was discussed.
New alkoxymethyl-functionalized pyridinium-based chiral ionic liquids: synthesis, characterization and properties
Gondal, Humaira Yasmeen,Mumtaz, Salma,Abbaskhan, Ahmed,Mumtaz, Nargis,Cano, Israel
, p. 2951 - 2963 (2020)
Abstract: An efficient solvent-free synthesis of a new family of functionalized chiral ionic liquids based on pyridinium cation has been developed from low-cost chiral terpenoid alcohols. An exhaustive characterization was performed using state-of-the-art
Synthesis of inexpensive chiral half-sandwich nickel N-heterocyclic carbene complexes: X-ray diffraction study of the D-menthyl-functionalized complex [Ni(iPr2Ph-NHC-CH2OMent)ClCp]
Rocquin, Mansuy,Ritleng, Vincent,Barroso, Sónia,Martins, Ana M.,Chetcuti, Michael J.
, p. 57 - 62 (2016)
The imidazolium salts, 1-(2,4,6-trimethylphenyl)-3-[(1R,2S,5R)-(?)-menthoxymethyl]imidazolium chloride (Mes-NHC-CH2OMent·HCl) (1a) and 1-(2,6-diisopropylphenyl)-3-[(1R,2S,5R)-(?)-menthoxymethyl]imidazolium chloride (iPr2Ph-NHC-CH2OMent·HCl) (1b), are readily accessible from inexpensive (1R,2S,5R)-(?)-menthol. They react with nickelocene to give two new chiral nickel-N-heterocyclic carbene (NHC) complexes, [Ni(Mes-NHC-CH2OMent)ClCp] (2a) and [Ni(iPr2Ph-NHC-CH2OMent)ClCp] (2b), in good yields. The new complexes were fully characterized by standard spectroscopic techniques and by a single crystal X-ray diffraction study on complex 2b. Complex 2b crystallizes in the chiral spacegroup P1, with two independent molecules in the unit cell, which are slightly different from each other. Preliminary studies show that these complexes are effective catalysts for the hydrosilylation of ketones. However no chiral induction was observed.
Chiral protic imidazolium salts with a (-)-menthol fragment in the cation: Synthesis, properties and use in the Diels-Alder reaction
Janus, Ewa,Gano, Marcin,Feder-Kubis, Joanna,So?nicki, Jacek
, p. 10318 - 10331 (2018/03/26)
New chiral protic imidazolium salts containing a (1R,2S,5R)-(-)-menthol substituent in the cation and four different anions (chloride, hexafluorophosphate, trifluoromethanesulfonate and bis(trifluoromethylsulfonyl)imide) were efficiently prepared and exte
