Synthesis and properties of ionic liquids based on 1-methyl-3-(2-phenethyl)imidazolium

The synthesis and properties of three ionic liquids based on 1-methyl-3-(2-phenethyl)imidazolium cation ([MPIm]) and the chloride, tetrafluoroborate, and hexafluorophosphate anions have been investigated. The proposed quaternization and anion exchange processes afforded quantitative amounts of the three ionic liquids, and very pure [MPIm][BF4] and [MPIm][PF6] were obtained after recrystallization from ethanol. [MPIm][BF4] showed low melting point and high electrical conductivity. These ionic liquids (immiscible with diethyl ether but miscible with water and DMSO) absorb air moisture, increasing their mass and decreasing their viscosity. The results of NMR spectroscopy (1H, 13C, and 19F) and X-ray structure determination confirm the possibility of ion-pair and hydrogen-bond formation in [MPIm][BF4].

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Synthesis of a Conformationally Stable Atropisomeric Pair of Biphenyl Scaffold Containing Additional Stereogenic Centers

Molecules ◽

10.3390/molecules24030643 ◽

2019 ◽

Vol 24 (3) ◽

pp. 643 ◽

Cited By ~ 1

Author(s):

Chi-Tung Yeung ◽

Wesley Chan ◽

Wai-Sum Lo ◽

Ga-Lai Law ◽

Wing-Tak Wong

Keyword(s):

Hydrogen Bond ◽

Intramolecular Hydrogen Bond ◽

Bond Formation ◽

Aldol Reaction ◽

Spatial Arrangement ◽

Hydroxyl Groups ◽

Hydrogen Bond Formation ◽

X Ray ◽

Stereogenic Centers ◽

Intramolecular Hydrogen

The synthesis of a new CF3-containing stereogenic atropisomeric pair of ortho-disubstituted biphenyl scaffold is presented. The atropisomers are surprisingly conformationally stable for isolation. X-ray structures show that their stability comes from an intramolecular hydrogen bond formation from their two hydroxyl groups and renders the spatial arrangement of their peripheral CF3 and CH3 groups very different. The synthesized stereogenic scaffold proved to be effective in catalyzing the asymmetric N-nitroso aldol reaction of enamine and nitrosobenzene. Compared to similar scaffolds without CF3 groups, one of our atropisomer exhibits an increase in enantioselectivity in this reaction.

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Chemistry of Diamino-Ligated Methylpalladium(II) Alkoxide Complexes: Syntheses, x-ray Crystal Structures, and Hydrogen-Bond Formation

Journal of the American Chemical Society ◽

10.1021/ja00149a017 ◽

1995 ◽

Vol 117 (44) ◽

pp. 10939-10949 ◽

Cited By ~ 35

Author(s):

Gerardus M. Kapteijn ◽

Athanasia Dervisi ◽

David M. Grove ◽

Huub Kooijman ◽

Miles T. Lakin ◽

...

Keyword(s):

Hydrogen Bond ◽

Crystal Structures ◽

Bond Formation ◽

Hydrogen Bond Formation ◽

X Ray

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Mechanisms of hydrogen bond formation between ionic liquids and cellulose and the influence of water content

Physical Chemistry Chemical Physics ◽

10.1039/c4cp04060k ◽

2015 ◽

Vol 17 (8) ◽

pp. 5767-5775 ◽

Cited By ~ 55

Author(s):

Brooks D. Rabideau ◽

Ahmed E. Ismail

Keyword(s):

Hydrogen Bond ◽

Hydrogen Bonding ◽

Ionic Liquids ◽

Water Content ◽

Complex Network ◽

Bond Formation ◽

Hydrogen Bond Formation ◽

Influence Of Water

We explore the complex network of transitions occurring between different hydrogen bonding states within ionic liquids and cellulose.

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Vapochromism induced by intermolecular electron transfer coupled with hydrogen-bond formation in zinc dithiolene complex

Journal of Materials Chemistry C ◽

10.1039/d0tc04280c ◽

2020 ◽

Vol 8 (42) ◽

pp. 14939-14947

Author(s):

So Yokomori ◽

Shun Dekura ◽

Tomoko Fujino ◽

Mitsuaki Kawamura ◽

Taisuke Ozaki ◽

...

Keyword(s):

Hydrogen Bond ◽

Electron Transfer ◽

Bond Formation ◽

Intermolecular Electron Transfer ◽

Hydrogen Bond Formation ◽

Complex Crystal

A novel vapochromic mechanism by intermolecular electron transfer coupled with hydrogen-bond formation was realized in a zinc dithiolene complex crystal.

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Diverse mechanisms of carbon-hydrogen bond formation through binuclear reductive elimination reactions

Journal of the American Chemical Society ◽

10.1021/ja00366a044 ◽

1982 ◽

Vol 104 (2) ◽

pp. 619-621 ◽

Cited By ~ 31

Author(s):

Mario J. Nappa ◽

Roberto Santi ◽

Steven P. Diefenbach ◽

Jack Halpern

Keyword(s):

Hydrogen Bond ◽

Bond Formation ◽

Reductive Elimination ◽

Hydrogen Bond Formation ◽

Elimination Reactions

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Theoretical analysis of the (HNO)2, (HNO···HNS), and (HNS)2 dimers — A case of red and blue shifts of N–H stretching frequency

Canadian Journal of Chemistry ◽

10.1139/v10-048 ◽

2010 ◽

Vol 88 (8) ◽

pp. 849-857 ◽

Cited By ~ 2

Author(s):

Nguyen Tien Trung ◽

Tran Thanh Hue ◽

Minh Tho Nguyen

Keyword(s):

Hydrogen Bond ◽

Quantum Chemical ◽

Bond Formation ◽

Blue Shift ◽

Proton Donor ◽

Basis Sets ◽

Coupled Cluster ◽

Hydrogen Bond Formation ◽

Length Contraction ◽

Moller Plesset

The hydrogen-bonded interactions in the simple (HNZ)2 dimers, with Z = O and S, were investigated using quantum chemical calculations with the second-order Møller–Plesset perturbation (MP2), coupled-cluster with single, double (CCSD), and triple excitations (CCSD(T)) methods in conjunction with the 6-311++G(2d,2p), aug-cc-pVDZ, and aug-cc-pVTZ basis sets. Six-membered cyclic structures were found to be stable complexes for the dimers (HNO)2, (HNS)2, and (HNO–HNS). The pair (HNS)2 has the largest complexation energy (–11 kJ/mol), and (HNO)2 the smallest one (–9 kJ/mol). A bond length contraction and a frequency blue shift of the N–H bond simultaneously occur upon hydrogen bond formation of the N–H···S type, which has rarely been observed before. The stronger the intramolecular hyperconjugation and the lower the polarization of the X–H bond involved as proton donor in the hydrogen bond, the more predominant is the formation of a blue-shifting hydrogen bond.

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