scholarly journals Liquid-assisted grinding and ion pairing regulates percentage conversion and diastereoselectivity of the Wittig reaction under mechanochemical conditions

2018 ◽  
Vol 14 ◽  
pp. 688-696 ◽  
Author(s):  
Kendra Leahy Denlinger ◽  
Lianna Ortiz-Trankina ◽  
Preston Carr ◽  
Kingsley Benson ◽  
Daniel C Waddell ◽  
...  
Keyword(s):  
Dielectric Constant ◽  
Chemical Reaction ◽  
Wittig Reaction ◽  
Ion Pairing ◽  
Mechanochemical Reaction ◽  
Grinding Balls ◽  
High Speeds ◽  
Counter Ion ◽  
Percentage Conversion

Mechanochemistry is maturing as a discipline and continuing to grow, so it is important to continue understanding the rules governing the system. In a mechanochemical reaction, the reactants are added into a vessel along with one or more grinding balls and the vessel is shaken at high speeds to facilitate a chemical reaction. The dielectric constant of the solvent used in liquid-assisted grinding (LAG) and properly chosen counter-ion pairing increases the percentage conversion of stilbenes in a mechanochemical Wittig reaction. Utilizing stepwise addition/evaporation of ethanol in liquid-assisted grinding also allows for the tuning of the diastereoselectivity in the Wittig reaction.

Ion Pairing, H-bonding, and π-π Interactions in Cobalt(II) Compound Containing Guanidinium Counter Ion

2006 ◽  
Vol 632 (3) ◽  
pp. 469-474 ◽  
Author(s):  
Shabnam Sheshmani ◽  
Hossein Aghabozorg ◽  
Fahimeh Mohammad Panah ◽  
Robabeh Alizadeh ◽  
Guido Kickelbick ◽  
...  
Keyword(s):  
Ion Pairing ◽  
Π Interactions ◽  
Counter Ion

Anionic polymerization of styrene in oxepane (hexamethylene oxide)•counter-ion, sodium

1970 ◽  
Vol 48 (13) ◽  
pp. 2031-2034 ◽  
Author(s):  
G. Löhr ◽  
S. Bywater
Keyword(s):  
Dielectric Constant ◽  
Dipole Moment ◽  
Rate Constant ◽  
Wide Temperature Range ◽  
Anionic Polymerization ◽  
Propagation Rate ◽  
Ion Pair ◽  
Temperature Range ◽  
Counter Ion ◽  
Propagation Rate Constant

The propagation reaction in the anionic polymerization of styrene in oxepane has been studied as a function of temperature and concentration of polystyrylsodium. Conductance measurements on polystyrylsodium were also made together with determinations of density, viscosity, dielectric constant, and dipole moment of oxepane itself. The measurements enabled the propagation rate constant to be determined of the polystyryl anion at 30 °C and of the ion-pair over a wide temperature range. The results have been compared with those obtained in tetrahydrofuran and tetrahydropyran.

Quaternary Phosphonium Carboxylates: Structure, Dynamics and Intriguing Olefination Mechanism

Synthesis ◽  
2021 ◽  
Author(s):  
Kirill Nikitin ◽  
Anna C. Vetter ◽  
Helge Müller-Bunz ◽  
Jimmy Muldoon
Keyword(s):  
Solid State ◽  
Wittig Reaction ◽  
Ion Pairing ◽  
Ion Pair ◽  
State Structure ◽  
Solid State Structure ◽  
Structure Dynamics ◽  
Complex Process

AbstractWe have earlier shown how the Wittig chemistry can be done using novel Eigenbase phosphonium carboxylate reagents. Here we discuss the phenomenon of ion pairing, their solution tautomerism, solid-state structure, and mechanistic aspects of olefination. The results point to a complex process involving unfamiliar H-bond-driven ion-pair equilibria followed by standard Wittig reaction steps.

The Volume Change on Ion-Pairing of Symmetrical Electrolytes

1983 ◽  
Vol 38 (2) ◽  
pp. 247-251 ◽  
Author(s):  
Y. Marcus
Keyword(s):  
Dielectric Constant ◽  
Molar Volume ◽  
High Precision ◽  
Partial Molar Volume ◽  
Volume Change ◽  
Isothermal Compressibility ◽  
Association Constant ◽  
Ambient Pressure ◽  
Pressure Coefficient ◽  
Ion Pairing

Abstract The increase in the standard partial molar volume of a symmetrical electrolyte on ion-pairing, ΔV∞, calculated from the experimental association constant at ambient pressure, the isothermal compressibility, the dielectric constant of the solvent and its pressure coefficient, is as good a measure of this quantity as values calculated from more elaborate experimental procedures, such as the pressure coefficient of the association constant or high precision density determinations in dilute solutions.

scholarly journals The effect of solvent on reactivity of the Li2S–P2S5 system in liquid-phase synthesis of Li7P3S11 solid electrolyte

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Hirotada Gamo ◽  
Atsushi Nagai ◽  
Atsunori Matsuda
Keyword(s):  
Dielectric Constant ◽  
Liquid Phase ◽  
Solid Electrolyte ◽  
Chemical Reaction ◽  
High Purity ◽  
Boiling Point ◽  
Chemical Properties ◽  
Phase Synthesis ◽  
Design For All ◽  
Wet Chemical

AbstractSynthesis technology for sulfide-based solid electrolytes based on liquid-phase processing has attracted significant interest in relation to achieving the optimal design for all-solid-state batteries. Herein, guidelines to solvent selection for the liquid-phase synthesis of superionic conductor Li7P3S11 are described through systematic examination. 70Li2S–30P2S5 system, a source of Li7P3S11, is treated via a wet chemical reaction using eight organic solvents with different physical and chemical properties (i.e., dielectric constant, molecule structure, and boiling point). We reveal that the solvent’s polarity, characterized by the dielectric constant, plays an important role in the formation of crystalline Li7P3S11 via wet chemical reaction. In addition, acetonitrile (ACN) solvent with a high dielectric constant was found to lead to high-purity crystalline Li7P3S11 and intrinsically high ionic conductivity. Further, solvents with a high boiling point and ring structures that cause steric hindrance were found to be unfavorable for the wet chemical synthesis of Li7P3S11 solid electrolyte. Overall, we demonstrate that ACN solvent is the most suitable for the liquid-phase synthesis of a crystalline Li7P3S11 solid electrolyte with high purity based on its dielectric constant, molecular structure, and boiling point.

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