Glymes as Versatile Solvents for Chemical Reactions and Processes: from the Laboratory to Industry.

Glymes, also known as glycol diethers, are saturated non-cyclic polyethers containing no other functional groups. Most glymes are usually less volatile and less toxic than common laboratory organic solvents; in this context, they are more environmentally benign solvents. However, it is also important to point out that some glymes could cause long-term reproductive and developmental damages despite their low acute toxicities. Glymes have both hydrophilic and hydrophobic characters that common organic solvents are lack of. In addition, they are usually thermally and chemically stable, and can even form complexes with ions. Therefore, glymes are found in a broad range of laboratory applications including organic synthesis, electrochemistry, biocatalysis, materials, and Chemical Vapor Deposition (CVD), etc. In addition, glyme are used in numerous industrial applications, such as cleaning products, inks, adhesives and coatings, batteries and electronics, absorption refrigeration and heat pumps, as well as pharmaceutical formulations, etc. However, there is a lack of comprehensive and critical review on this attractive subject. This review aims to accomplish this task by providing an in-depth understanding of glymes' physicochemical properties, toxicity and major applications.

[1]  M. A. Rivas,et al.  Permittivity and density of the systems (monoglyme, diglyme, triglyme, or tetraglyme + n-heptane) at several temperatures , 2011 .

[2]  S. Kauzlarich,et al.  Investigation of reaction conditions for optimal germanium nanoparticle production by a simple reduction route , 2006 .

[3]  Chang Won Yoon,et al.  Ammonia triborane: a new synthesis, structural determinations, and hydrolytic hydrogen-release properties. , 2009, Journal of the American Chemical Society.

[4]  A. Hvidt,et al.  Densities and derived volume functions of binary mixtures: (an ethylene glycol derivative + water) at 298.15 K , 1985 .

[5]  P. Flory,et al.  Optical anisotropies of polyoxyethylene oligomers , 1972 .

[6]  E. Hessell,et al.  Substitution of unactivated aryl halides by thiolate anions in polyglymes , 1985 .

[7]  J. L. Legido,et al.  Study of static permittivity and density of the systems {(n-nonane + monoglyme or diglyme)} at various temperatures , 2009 .

[8]  F. Rossi,et al.  Direct fabrication of nanoscale bio-adhesive patterns by electron beam surface modification of plasma polymerized poly ethylene oxide-like coatings , 2008, Nanotechnology.

[9]  J. St-Arnaud,et al.  Dielectric constants of acetonitrile, γ-butyrolactone, propylene carbonate, and 1,2-dimethoxyethane as a function of pressure and temperature , 1996 .

[10]  Solution preparation of Ge nanoparticles with chemically tailored surfaces , 2002 .

[11]  M. Newman,et al.  Reactions of 5,5-disubstituted 3-nitrosooxazolidones. New syntheses of vinyl azides, vinyl isothiocyanates, vinyl diethyl phosphonates, and divinyl ethers , 1973 .

[12]  E. Carballo,et al.  Excess Molar Volumes and Excess Molar Heat Capacities of Mixtures Containing (Mono and Poly)ethers + Ethyl Acetate , 1997 .

[13]  W. Henderson,et al.  Raman study of crystalline solvates between glymes CH3(OCH2CH2)nOCH3(n = 1, 2 and 3) and LiClO4 , 2004 .

[14]  R. Fernández-Lafuente,et al.  A criterion for the selection of monophasic solvents for enzymatic synthesis , 1998 .

[15]  J. S. Beck,et al.  Thermally induced borazine dehydropolymerization reactions. Synthesis and ceramic conversion reactions of a new high-yield polymeric precursor to boron nitride , 1990 .

[16]  Y. Shotland,et al.  Glycerol as a green solvent for high product yields and selectivities , 2007 .

[17]  J. A. Reeder,et al.  Thermal dissociation of aryl carbanilates in glyme , 1971 .

[18]  R. Gandour,et al.  THE REMARKABLE CATALYTIC POWER OF GLYMES IN ESTER AMINOLYSIS CARRIED OUT IN NONPOLAR MEDIA , 1980 .

[19]  H. Walborsky,et al.  Cyclopropanes. XXX. Reductive cleavage of cyclopropane rings , 1971 .

[20]  David J. Williams,et al.  Monomeric Group IIA metal .beta.-diketonates stabilized by multidentate glymes , 1993 .

[21]  G. Karlstróm,et al.  Conformational structure of 1,2-dimethoxyethane in water and other dipolar solvents, studied by quantum chemical, reaction field, and statistical mechanical techniques , 1985 .

[22]  R. Rieke,et al.  Highly reactive metallic nickel: reductive homocoupling reagent for benzylic mono- and polyhalides , 1984 .

[23]  C. Pittman,et al.  Dechlorination of polychlorobiphenyls using NaBH4 and NaBH4/LiCl at 120–310°C in glyme solvents , 2001 .

[24]  L. Sneddon,et al.  Microstructure and Indentation Fracture Behavior of SiC−BN Composites Derived from Blended Precursors of AHPCS and Polyborazylene , 2004 .

[25]  J. Mejuto,et al.  A new reaction pathway in the ester aminolysis catalyzed by glymes and crown ethers. , 2006, The Journal of organic chemistry.

[26]  R. Lagow,et al.  Group IIB (12) metal alkyls: the synthesis of trifluorosilyl and trifluoromethyl alkyls of cadmium and zinc , 1986 .

[27]  B. Lu,et al.  Excess volumes for binary mixtures formed by 2,5,8,11-tetraoxadodecane or 2,5,8,11,14-pentaoxapentadecane with homologous n-alkanes , 1990 .

[28]  R. Gandour,et al.  Fingerprinting a transition-structure guest by a building-block approach with an incremental series of catalytic hosts. Structural requirements for glyme and .alpha.,.omega.-dimethoxyalkane catalyses in N-methylbutylaminolysis and butylaminolysis of 4-nitrophenyl acetate in chlorobenzene , 1992 .

[29]  Jie Wu,et al.  Phenyliodonium zwitterion as an efficient electrophile in the palladium-catalyzed suzuki-type reaction: a novel method for the synthesis of 3-aryl-4-hydroxycoumarins. , 2002, Organic letters.

[30]  D. Bedrov,et al.  Molecular dynamics simulations of 1,2-dimethoxyethane in aqueous solution: Influence of the water potential , 1999 .

[31]  D. Naumann,et al.  Neue Syntheseverfahren für Nitrosoperfluoralkane CnF2n+1NO (n=1, 2, 3, 6) , 1995 .

[32]  P. Johansson,et al.  Modelling amorphous lithium salt–PEO polymer electrolytes: ab initio calculations of lithium ion–tetra-, penta- and hexaglyme complexes , 1999 .

[33]  M. Meot-ner The ionic hydrogen bond. 2. Intramolecular and partial bonds. Protonation of polyethers, crown ethers, and diketones , 1983 .

[34]  K. Kusano Densities, refractive indexes, and normal boiling points of 1,2-disubstituted ethylene glycol derivatives , 1978 .

[35]  J. Larson,et al.  Developmental toxicity and structure/activity correlates of glycols and glycol ethers. , 1984, Environmental health perspectives.

[36]  P. G. Gassman,et al.  The Cleavage of Nonenolizable Ketones , 1967 .

[37]  R. Niemeier,et al.  Genetic effects of 2-methoxyethanol and bis(2-methoxyethyl)ether. , 1983, Toxicology and applied pharmacology.

[38]  J. Miller,et al.  Chemistry of Enolates .7. Kinetics and Orientation in Dimethyl Sulfoxide - Relative Nucleophilicities of Enolates , 1971 .

[39]  Christopher P. Rhodes,et al.  Local structures in crystalline and amorphous phases of Diglyme-LiCF3SO3 and poly(ethylene oxide)-LiCF3SO3 systems : Implications for the mechanism of ionic transport , 2001 .

[40]  J. C. Reis,et al.  Kirkwood correlation factors in liquid mixtures from an extended Onsager-Kirkwood-Fröhlich equation. , 2011, Physical chemistry chemical physics : PCCP.

[41]  J. González,et al.  Excess molar volumes of 1-propanol + n-polyethers at 298.15 K , 1997 .

[42]  N. Hosmane,et al.  High yield preparation of the tetradecahydroundecaborate(1-) anion, [B11H14]-, from pentaborane(9) , 1987 .

[43]  G. Stork,et al.  Generation, nuclear magnetic resonance spectra, and alkylation of enolates from trialkylsilyl enol ethers , 1968 .

[44]  M. Watanabe,et al.  Physicochemical Properties of Glyme–Li Salt Complexes as a New Family of Room-temperature Ionic Liquids , 2010 .

[45]  M. Costas,et al.  Effect of molecular size on the W-shaped excess heat capacities: oxaalkane–alkane systems , 1991 .

[46]  Hiroyuki Ohno,et al.  Long-term stability of conformation and redox response of cross-linked cytochrome c in polymer solvent , 2000 .

[47]  C. Carvajal,et al.  Studies of Solvation Phenomena of Ions and Ion Pairs in Dimethoxyethane and Tetrahydrofuran , 1965 .

[48]  W. Henderson,et al.  Glyme−Lithium Bis(trifluoromethanesulfonyl)imide and Glyme−Lithium Bis(perfluoroethanesulfonyl)imide Phase Behavior and Solvate Structures , 2005 .

[49]  W. Henderson,et al.  Glyme-lithium salt phase behavior. , 2006, The journal of physical chemistry. B.

[50]  B. P. Sullivan,et al.  Synthesis of closo- and nido-metalloboranes from metallocenes , 1978 .

[51]  K. Vollhardt,et al.  Further studies on hydration of alkynes by the PtCl4-CO catalyst , 2002 .

[52]  Scott Lynn,et al.  Solubility of hydrogen sulfide, sulfur dioxide, carbon dioxide, propane, and n-butane in poly(glycol ethers) , 1988 .

[53]  H. K. Frensdorff Stability constants of cyclic polyether complexes with univalent cations , 1971 .

[54]  J. Schomaker,et al.  The synthesis of substituted phenylpyrimidines via suzuki coupling reactions , 2006 .

[55]  I. Fragalà,et al.  Volatile CeIII Hexafluoroacetylacetonate Glyme Adducts as Promising Precursors for the MOCVD of CeO2 Thin Films , 2000 .

[56]  Doron Aurbach,et al.  The study of electrolyte solutions based on solvents from the “glyme” family (linear polyethers) for secondary Li battery systems , 1997 .

[57]  S. Tseregounis,et al.  Solubility of HFC‐134a refrigerant in glycol‐type compounds: Effects of glycol structure , 1994 .

[58]  Josefa Fernández,et al.  Volumetric Properties of Monoethylene Glycol Dimethyl Ether and Diethylene Glycol Dimethyl Ether up to 60 MPa , 2003 .

[59]  D. Aurbach,et al.  Electrolyte Solutions for Rechargeable Magnesium Batteries Based on Organomagnesium Chloroaluminate Complexes , 2002 .

[60]  N. Brown,et al.  Inhibitors of Bacillus subtilis DNA polymerase III. 6-(arylalkylamino)uracils and 6-anilinouracils. , 1977, Journal of medicinal chemistry.

[61]  Arno Behr,et al.  Improved utilisation of renewable resources: New important derivatives of glycerol , 2008 .

[62]  J. D. Lamb,et al.  Thermodynamic and kinetic data for cation-macrocycle interaction , 1985 .

[63]  K. Murakami,et al.  1H NMR Studies on the Interactions of Acyclic Polyethers with Dimethyltin Bichloride in Aromatic Solvents , 1981 .

[64]  Masahiro Kato,et al.  Vapor-liquid equilibrium determination by total pressure measurements for three binary systems made of 1,2-dimethoxyethane with toluene, methylcyclohexane, or (trifluoromethyl)benzene , 1991 .

[65]  D. Bedrov,et al.  Anomalous conformational behavior of poly(ethylene oxide) oligomers in aqueous solutions. a molecular dynamics study , 1998 .

[66]  A. Pal,et al.  Temperature Dependence of the Volumetric Properties of Binary Mixtures Containing Polyethers and 1-Propanol , 2003 .

[67]  I. Fragalà,et al.  Europium “Second Generation” Precursors for Metal‐Organic Chemical Vapor Deposition: Characterization and Optical Spectroscopy , 2001 .

[68]  S. Scheiner,et al.  The Ionic Hydrogen Bond. 5. Polydentate and Solvent-Bridged Structures. Complexing of the Proton and the Hydronium Ion by Polyethers , 1994 .

[69]  L. W. Sieck,et al.  Thermal decomposition of ions. 1. Pyrolysis of protonated ethers. Activation energies and A factors , 1984 .

[70]  C. Pittman,et al.  Dechlorination of Pentachlorophenol and 1,2,4-Trichlorobenzene Using NaBH4 and NaBH4/LiCl AT 125–315°C in Glyme Solvents , 1998 .

[71]  W. Henderson,et al.  LiClO4 Electrolyte Solvate Structures , 2004 .

[72]  François Jérôme,et al.  Glycerol as a sustainable solvent for green chemistry , 2010 .

[73]  S. Tobishima,et al.  Influence of glyme-based nonaqueous electrolyte solutions on electrochemical properties of Si-based anodes for rechargeable lithium cells , 2006 .

[74]  D. Brouillette,et al.  Apparent Molar Volume, Heat Capacity, and Conductance of Lithium Bis(trifluoromethylsulfone)imide in Glymes and Other Aprotic Solvents , 1998 .

[75]  D. Mingos,et al.  Facile synthesis of alkaline-earth-metal β-diketonates and thestructure of the loose dimer[{Ca(hfpd)2}2(heptaglyme)][hfpd = F3CCOCHCOCF3 andheptaglyme = Me(OCH2CH2)7OMe)] , 1997 .

[76]  J. Smid,et al.  Complexation of lithium, sodium, and potassium carbanion pairs with polyglycol dimethyl ethers (glymes). Effect of chain length and temperature , 1970 .

[77]  Hua Zhao,et al.  Glymes as benign co-solvents for CaO-catalyzed transesterification of soybean oil to biodiesel. , 2013, Bioresource technology.

[78]  S. Beltrán,et al.  Isobaric vapor-liquid equilibrium data for the binary systems 1,2-dimethoxyethane + alcohols , 1991 .

[79]  C. A. Reilly,et al.  Cobalt-catalysed reaction of carbon monoxide–hydrogen mixtures in alkoxy-terminated polyglycol solvents , 1981 .

[80]  L. Krause,et al.  Trifluoromethyl group 2B compounds: bis(trifluoromethyl)cadmium.base. New, more powerful ligand-exchange reagents and low-temperature difluorocarbene sources , 1981 .

[81]  G. Baker,et al.  Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications. , 2012, Chemical Society reviews.

[82]  G. W. Canters Sodium-23 nuclear magnetic resonance on sodium borate solutions. Anion, solvent, and viscosity effects , 1972 .

[83]  D. Mcgregor Genotoxicity of glycol ethers. , 1984, Environmental health perspectives.

[84]  G. López,et al.  Molecular adsorption and the chemistry of plasma-deposited thin organic films: Deposition of oligomers of ethylene glycol , 1996 .

[85]  Ian D. Williams,et al.  Higher coordinate complexes. 23. Reductive coupling of carbon monoxide ligands to form coordinated bis(trimethylsiloxy)ethyne in seven-coordinate niobium(I) and tantalum(I) [M(CO)2(dmpe)2Cl] complexes , 1987 .

[86]  G. Bernardinelli,et al.  H-bonded polymer structures of different dimensionality: syntheses and crystal structures of [Ca(DME)n(H2O)m]I2·(DME)x (1: n=3, m=3, x=1; 2: n=2, m=4, x=0) and [Ca{CH3(OCH2)3OCH3}(H2O)4]I2 , 2000 .

[87]  Masahiro Kato,et al.  Density, viscosity, and solubility of carbon dioxide in glymes , 2011 .

[88]  M. Watanabe,et al.  Reversibility of electrochemical reactions of sulfur supported on inverse opal carbon in glyme-Li salt molten complex electrolytes. , 2011, Chemical communications.

[89]  J. Mejuto,et al.  Influence of glymes upon percolative phenomena in AOT-based microemulsions. , 2005, Journal of colloid and interface science.

[90]  W. J. Wallace,et al.  Densities, refractive indexes, molar refractions, viscosities, and dielectric constants of triethylene glycol dimethyl ether-water solutions at 25.degree. , 1968 .

[91]  Chein-Hsiun Tu,et al.  Densities and Viscosities of Seven Glycol Ethers from 288.15 K to 343.15 K , 2000 .

[92]  Jaephil Cho Control of the carbon shell thickness in Sn70Ge30@carbon core-shell nanoparticles using alkyl terminators : Its implication for high-capacity lithium battery anode materials , 2008 .

[93]  P. Johansson First principles modelling of amorphous polymer electrolytes: Li+–PEO, Li+–PEI, and Li+–PES complexes , 2001 .

[94]  A. Okamoto,et al.  Effect of Polymer as Cosolvent on Chemical Reactions in Solution III. Thermodynamical Cosolvent Effect of Glymes on the Reaction of Dansyl Chloride with Butylamine in Chloroform , 1983 .

[95]  A. Coronas,et al.  Liquid Densities, Kinematic Viscosities, and Heat Capacities of Some Ethylene Glycol Dimethyl Ethers at Temperatures from 283.15 to 423.15 K , 1998 .

[96]  A. Maccioni,et al.  Catalytic activity of cyclophosphazenic polypodands in phase-transfer reactions. Comparison with open-chain analogues. , 1991 .

[97]  D. Awschalom,et al.  Kinetic-Dependent Crystal Growth of Size-Tunable CdS Nanoparticles , 2001 .

[98]  T. Fuchigami,et al.  Electrolytic Partial Fluorination of Organic Compounds. Part 41: Highly Selective Electrolytic Fluorination of Dimethoxyethane, its Homologues, and Crown Ethers , 2000 .

[99]  Y. Katayama,et al.  Lithium dope and undope reactions for tin in an ionic liquid electrolyte with some glymes , 2010 .

[100]  T. Hanusa,et al.  A reinvestigation of the reaction of arylcalcium iodides with nitrous oxide , 1995 .

[101]  P. Johansson,et al.  Local coordination and conformation in polyether electrolytes : geometries of M-triglyme complexes (M = Li, Na, K, Mg and Ca) from ab-initio molecular orbital calculations , 1996 .

[102]  R. Manderville,et al.  Ambident nucleophilic reactivity. 9. Regioselectivity in the reaction of ambident phenoxide ion and methoxide and hydroxide ions with 2,4,6-trinitroanisole. Kinetic and thermodynamic control , 1992 .

[103]  B. Phillips,et al.  Synthesis and Characterization of Sn/R, Sn/Si−R, and Sn/SiO2 Core/Shell Nanoparticles , 2000 .

[104]  J. Smid,et al.  Effect of solvation on the reactivity of ion pairs , 1968 .

[105]  S. Daniele,et al.  Hydrolysis of a (2-Propanol)yttrium Triiodide Complex in the Presence of Glymes: Synthesis and X-ray Structures of Hydroxo-Bridged Dinuclear Yttrium Complexes and Their Applications in Materials Science , 2007 .

[106]  Christopher P. Rhodes,et al.  Crystalline phases of poly(ethylene oxide) oligomers and sodium triflate: Changes in coordination and conformation with chain length , 2002 .

[107]  J. Mahía,et al.  Outer-sphere addition compounds of MoO2Br2(H2O)2 with ethers. Molecular structure of MoO2Br2(H2O)2·L (L=2,5,8-trioxanonane; 2,5,8,11,14-pentaoxapentadecane) , 2001 .

[108]  I. Fragalà,et al.  New Thermally Stable and Highly Volatile Precursors for Lanthanum MOCVD: Synthesis and Characterization of Lanthanum .beta.-Diketonate Glyme Complexes , 1995 .

[109]  A. Burgen,et al.  Spin-lattice relaxation of methyl protons in some compounds of biological interest. , 1969, Journal of the American Chemical Society.

[110]  J. Smith,et al.  W-shape excess heat capacities, upper critical solution temperatures and non-randomness in oligomeric oxaalkane–dimethylsiloxane systems , 1992 .

[111]  M. Salomon,et al.  Conductivities of 1∶1 salts in 2-cyanopyridine , 1994 .

[112]  J. C. Reis,et al.  Aggregative processes in aqueous solutions of mono- to tetra-ethylene glycol dimethyl ether at 298.15 K , 2004 .

[113]  M. Villamañán,et al.  Calorimetric investigation of the interactions between oxygen and hydroxyl groups in (alcohol+ether) at 298.15 K☆☆☆ , 1982 .

[114]  Pedro J. Bernal,et al.  Apparent Molar Volumes and Adiabatic Compressibilities of Crown Ethers and Glymes in H2O and D2O at 25°C , 2001 .

[115]  G. C. Fu,et al.  Nickel-catalyzed asymmetric cross-couplings of racemic propargylic halides with arylzinc reagents. , 2008, Journal of the American Chemical Society.

[116]  D. Teeters,et al.  The concentration behavior of lithium triflate at the surface of polymer electrolyte materials , 1996 .

[117]  R. Rieke,et al.  Preparation, characterization, and chemistry of activated cobalt , 1986 .

[118]  M. E. Fragalá,et al.  Neodymium β-diketonate glyme complexes: Synthesis and characterization of volatile precursors for MOCVD applications , 2009 .

[119]  Linda F. Nazar,et al.  Positive Electrode Materials for Li-Ion and Li-Batteries† , 2010 .

[120]  Y. Kimura,et al.  Poly(ethylene glycols) are extraordinary catalysts in liquid-liquid two-phase dehydrohalogenation , 1982 .

[121]  R. Rieke,et al.  Monohomocyclooctatetraene Anion Radical. A Homoaromatic Nine-Electron System1,2 , 1966 .

[122]  A. Pal,et al.  Excess molar volumes and viscosities of 1-propanol + ethylene glycol, + ethylene glycol monomethyl, + ethylene glycol dimethyl, + diethylene glycol dimethyl, + triethylene glycol dimethyl, + diethylene glycol diethyl, and + diethylene glycol dibutyl ethers at 298.15 K , 1998 .

[123]  J. C. Gage,et al.  The subacute inhalation toxicity of 109 industrial chemicals , 1970 .

[124]  Q. K. Timerghazin,et al.  Oxidation of ethers with dimethyldioxirane , 2005 .

[125]  A novel method for the determination of a PCB sum value by enzyme immunoassay to overcome the cross-reactivity problem , 1999 .

[126]  David J. Williams,et al.  Lanthanide β-diketonate glyme complexes exhibiting unusual co-ordination modes , 1993 .

[127]  M. I. Andrade,et al.  Excess heat capacities of glyme[ndash ]alkane mixtures Influence of the upper critical solution temperature , 1997 .

[128]  Doron Aurbach,et al.  A short review on the comparison between Li battery systems and rechargeable magnesium battery technology , 2001 .

[129]  E. Arancibia,et al.  Excess molar volumes and viscosities of binary mixtures of bis(2-methoxyl)ether (diglyme) with chloroalkanes at 298.15 K , 1994 .

[130]  R. J. Ouellette,et al.  Oxidation by palladium(II). II. Products of the oxidation and isomerization of phenylcyclopropane by palladium(II) , 1971 .

[131]  D. Bedrov,et al.  Quantum-Chemistry-Based Force Field for 1,2-Dimethoxyethane and Poly(ethylene oxide) in Aqueous Solution , 1998 .

[132]  Protonation of polyethers, glymes, and crown ethers in the gas phase , 1984 .

[133]  Hua Zhao,et al.  Glymes as new solvents for lipase activation and biodiesel preparation. , 2013, Bioresource technology.

[134]  R. Fujishiro,et al.  The Dipole Moments of the Oligether of Ethylene Glycol , 1966 .

[135]  M. Kumaran,et al.  Thermodynamic properties for 2, 5, 8, 11-tetraoxadodecane + n-dodecane mixtures at 298.15 K , 1985 .

[136]  F. Rossi,et al.  Fouling and non-fouling surfaces produced by plasma polymerization of ethylene oxide monomer. , 2006, Acta biomaterialia.

[137]  H. Matsuura,et al.  Anomalous conformational behavior of short poly(oxyethylene) chains in water: An FT-IR spectroscopic study , 1995 .

[138]  C. Reichardt,et al.  Solvatochromic Dyes as Solvent Polarity Indicators , 1994 .

[139]  Howard W. H. Lee,et al.  Solution Synthesis of Germanium Nanocrystals Demonstrating Quantum Confinement , 1998 .

[140]  Giacomo Ceccone,et al.  Functional Micropatterned Surfaces by Combination of Plasma Polymerization and Lift-Off Processes , 2006 .

[141]  J. R. Briggs The selective trimerization of ethylene to hex-1-ene , 1989 .

[142]  P. Laszlo,et al.  Coordinating Abilities Towards Sodium of Oxygenated Solvents , 1976 .

[143]  J. Jagur-grodzinski,et al.  Protonation of macrocyclic polyethers. Complexes with hydrogen bromide and hydrogen tribromide in chloroform , 1972 .

[144]  A. L. Mathews,et al.  Densities, Refractive Indices, Molar Refractions, and Viscosities of Ethylene Glycol Dimethyl Ether-Water Solutions at 25°. , 1963 .

[145]  H. Brown,et al.  Improved procedures for the generation of diborane from sodium borohydride and boron trifluoride. , 2000, Inorganic chemistry.

[146]  A. Treszczanowicz,et al.  Excess isobaric thermal expansion in the systems formed by oligooxaethylene and alkane in terms of an associated mixture model with equation of state contribution , 1998 .

[147]  S. Moon,et al.  Thermal Decomposition Mechanism of Bis(dipivaloylmethanato)strontium Compounds Containing Glyme Adducts , 2003 .

[148]  P. Bruce,et al.  Crystalline small-molecule electrolytes. , 2007, Angewandte Chemie.

[149]  R. Lagow,et al.  A new trifluorosilyl exchange reagent: reactions of Cd(SiF3)2•glyme (glyme= dimethoxyethane) with dibromo metal phosphine complexes of platinum, palladium, and nickel yield trifluorosilyl substituted dialkyl compounds , 1990 .

[150]  Carlos Segovia Fernández,et al.  Temperature and Pressure Dependences of Thermophysical Properties of Some Ethylene Glycol Dimethyl Ethers from Ultrasonic Measurements , 2006 .

[151]  D. Dearden,et al.  Fundamental factors controlling the exchange of multidentate ligands: displacement of 12-crown-4 and triglyme from complexes with divalent alkaline earth cations , 2000 .

[152]  G. C. Fu,et al.  Catalytic asymmetric Hiyama cross-couplings of racemic alpha-bromo esters. , 2008, Journal of the American Chemical Society.

[153]  D. Awschalom,et al.  Growth of CdS Nanorods in Nonionic Amphiphilic Triblock Copolymer Systems , 2002 .

[154]  W. J. Wallace,et al.  Densities, viscosities, refractive indexes, and molar refractions of the binary system tetraethylene glycol dimethyl ether-water at 25.degree.C , 1983 .

[155]  D. Berkowitz,et al.  Hydrolytic enzymatic transformation of advanced synthetic intermediates: On the choice of the organic cosolvent , 1999 .

[156]  K. Takeyama,et al.  Li+ adsorption on a metal electrode from glymes , 1998 .

[157]  A. Illanes,et al.  Kinetically controlled synthesis of ampicillin with immobilized penicillin acylase in the presence of organic cosolvents , 2001 .

[158]  P. Fanwick,et al.  Reactions of the dirhenium(II) complexes Re2Cl4(PR3)4 with lithium aluminum hydride. A convenient synthetic route to the dirhenium octahydride complexes Re2H8(PR3)4 , 1989 .

[159]  C. Tsvetanov,et al.  Interactions of ligands with lithium picrate in dioxane , 1990 .

[160]  K. Izutsu,et al.  Potentiometric study of complexation and solvation of lithium ions in some solvents related to lithium batteries , 1996 .

[161]  B. Ratner,et al.  Plasma deposition and surface characterization of oligoglyme, dioxane, and crown ether nonfouling films. , 2005, Langmuir : the ACS journal of surfaces and colloids.

[162]  A. Maccioni,et al.  Cyclophosphazenic polypodands: a new class of powerful metal cation complexing agents and phase-transfer catalysts , 1989 .

[163]  E. Winterfeldt,et al.  Biogenetically patterned stereoselective total synthesis of the indole alkaloid roxburghine D , 1972 .

[164]  R. Gandour,et al.  Structural requirements for glyme catalysis in butylaminolysis of aryl acetates in chlorobenzene. Identification of -OCH2CH2OCH2CH2OCH2CH2O- as the optimal subunit for catalysis , 1991 .

[165]  R. Lagow,et al.  Synthesis and X-ray crystal structures of [Au(CH2)2PPh2]2(CF3)2, [Au(CH2)2PPh2]2(C6F5)2, and [PPN][Au(C6F5)4]: two dinuclear gold(II) ylide complexes containing alkyl and aryl ligands and a tetrakis(pentafluorophenyl)aurate(III) anion complex , 1987 .

[166]  V. F. Anufriev,et al.  Catalytic Activity of Diethylene Glycol Dimethyl Ethers in Conversion of 6,7-Dichloro-3-ethyl-2-ethoxynaphthazarine into Echinochrome Trimethyl Ether , 2002 .

[167]  G. J. Conard,et al.  Synthesis of N‐(2‐piperidylmethyl)‐2,5‐BIS(2,2,2‐trifluoroethoxy)benzamide‐carbonyl‐14C acetate (flecainide‐14C acetate) , 1981 .

[168]  J. Wermer,et al.  Pentaborane(9) as a source for higher boron hydride systems. A new synthesis of nido-5,6-dimethyl-5,6-dicarbaoctaborane(10) , 1986 .

[169]  J. Imbach,et al.  Solid-Liquid Phase-Transfer Catalysis I: Studies of the N-Alkylation of Purines and Pyrimidines , 1991 .

[170]  N. Browning,et al.  Room temperature synthesis of surface-functionalised boron nanoparticles. , 2007, Chemical communications.

[171]  J. Saavedra REDUCTION OF NITROSOAMIDES TO ALCOHOLS USING SODIUM BOROHYDRIDE , 1979 .

[172]  G. Canters,et al.  Investigations on single crystals of alkali+ biphenyl- radical salts , 1970 .

[173]  J. Vidal [Rh10As(CO)22]3-. Example of encapsulation of arsenic by transition-metal carbonyl clusters as illustrated by the structural study of the benzyltriethylammonium salt , 1981 .

[174]  J. Vidal,et al.  [Rh17(S)2(CO)32]3-. 1. An example of encapsulation of chalcogen atoms by transition-metal-carbonyl clusters. , 1978 .

[175]  J. Smid,et al.  Contact and solvent-separated ion pairs of carbanions. V. The role of solvent structure in alkali ion solvation , 1968 .

[176]  Y. Aihara,et al.  Pulse-Gradient Spin-Echo (1)H, (7)Li, and (19)F NMR Diffusion and Ionic Conductivity Measurements of 14 Organic Electrolytes Containing LiN(SO2CF3)2. , 1999, The journal of physical chemistry. B.

[177]  Donald G. Lee,et al.  Oxidation of hydrocarbons. 8. Use of dimethyl polyethylene glycol as a phase transfer agent for the oxidation of alkenes by potassium permanganate , 1978 .

[178]  G. Gokel,et al.  Structural parameters that control association constants between polyether host and alkylammonium guest compounds , 1974 .

[179]  P. Stang,et al.  Unsaturated carbenes from primary vinyl triflates. 7. Reaction with azoarenes , 1977 .

[180]  P. Bruce,et al.  Structure and Conductivity of Small-Molecule Electrolytes [CH3O(CH2CH2O)nCH3]:LiAsF6 (n = 8−12) , 2008 .

[181]  K. Hardcastle,et al.  Carbenoid reactions of 2-halomethyl-4,6-dimethyl-s-triazines. , 2002, The Journal of organic chemistry.

[182]  J. Abboud,et al.  Critical compilation of scales of solvent parameters. Part I. Pure, non-hydrogen bond donor solvents , 1999 .

[183]  Y. Kishi,et al.  Terminal epoxidation of farnesate attached to helical peptides. , 1986, Journal of the American Chemical Society.

[184]  P. Fanwick,et al.  A general synthetic route to the dirhenium octahydrides Re2H8(PR3)4 from the triply bonded complexes Re2Cl4(PR3)4. An unexpected structure for the complex Re2H8(dppm)2 (dppm = Ph2PCH2PPh2) , 1989 .

[185]  E. Rusanov,et al.  The Aza Curtius Rearrangement , 2001 .

[186]  M. Watanabe,et al.  Change from Glyme Solutions to Quasi-ionic Liquids for Binary Mixtures Consisting of Lithium Bis(trifluoromethanesulfonyl)amide and Glymes , 2011 .

[187]  Josefa Fernández,et al.  Pressure and Temperature Dependence of Excess Enthalpies of Methanol + Tetraethylene Glycol Dimethyl Ether and Methanol + Polyethylene Glycol Dimethyl Ether 250 , 1999 .

[188]  A. Spek,et al.  Complexation of bis(p-tert-butylphenyl)magnesium with 1,3-xylylene crown ethers and glymes , 1994 .

[189]  J. Tübke,et al.  Photocalorimetric monitoring of the polymerization of an oligo(ethylene glycol) dimethacrylate in oligo(ethylene glycol) dimethyl ethers , 1997 .

[190]  S. P. Gejji,et al.  Theoretical investigations on structure, electrostatics potentials and vibrational frequencies of Li+–CH3–O–(CH2–CH2–O)n–CH3(n  =  3–7) conformers , 2006 .

[191]  P. Bruce,et al.  Doping crystalline polymer electrolytes with glymes , 2007 .

[192]  D. K. Hazra,et al.  Density and viscosity for propylene carbonate + 1,2-dimethoxyethane at 298.15, 308.15, and 318.15 K , 1994 .

[193]  Susan M. Kauzlarich,et al.  Synthesis of Alkyl-Terminated Silicon Nanoclusters by a Solution Route , 1999 .

[194]  Doron Aurbach,et al.  Nonaqueous magnesium electrochemistry and its application in secondary batteries. , 2003, Chemical record.

[195]  M. Armand,et al.  Sulfamides and Glymes as Aprotic Solvents for Lithium Batteries , 1998 .

[196]  I. Fragalà,et al.  Yttrium β-Diketonate Glyme MOCVD Precursors: Effects of the Polyether Length on Stabilities, Mass Transport Properties and Coordination Spheres , 2004 .

[197]  R. V. Stevens,et al.  General methods of alkaloid synthesis. A new approach to the synthesis of the 5,10b-ethanophenanthridine Amaryllidaceae alkaloids. The total synthesis of (±)-3-epi-elwesine , 1970 .

[198]  J. Mejuto,et al.  Novel catalytic effects in ester aminolysis in chlorobenzene. , 2005, Chemical communications.

[199]  Kazuki Yoshida,et al.  New glyme–cyclic imide lithium salt complexes as thermally stable electrolytes for lithium batteries , 2010 .

[200]  I. Yonezu,et al.  Lanthanoid Nitrate Complexes with Some Polyethylene Glycols and Glymes , 1983 .

[201]  H. Ohno,et al.  Induced thermostability of poly(ethylene oxide)-modified hemoglobin in glycols. , 1997, Bioconjugate chemistry.

[202]  R. M. Izatt,et al.  Thermodynamic origin of the macrocyclic effect in crown ether complexes of sodium(1+), potassium(1+), and barium(2+) , 1982 .

[203]  Jack M. Miller,et al.  A study of metal chelation of dinucleotide analogs in the gas phase by fast-atom bombardment mass spectrometry , 1996, Journal of the American Society for Mass Spectrometry.

[204]  R. Manderville,et al.  Ambident reactivity of aryloxide ions towards 1,3,5-trinitrobenzene, low-temperature characterization of the elusive oxygen-bonded σ-complexes by 1H and 13C NMR spectroscopy , 1993 .

[205]  Ikchoon Lee,et al.  Nucleophilic Substitution Reactions of Thiophenyl 4-Nitrobenzoates with Pyridines in Acetonitrile. , 1999, The Journal of organic chemistry.

[206]  I. Fragalà,et al.  Synthesis, Characterization, Crystal Structure and Mass Transport Properties of Lanthanum β-Diketonate Glyme Complexes, Volatile Precursors for Metal−Organic Chemical Vapor Deposition Applications , 1998 .

[207]  K. Fromm,et al.  Polyether Adducts of d‐Block Metal Compounds as Starting Materials for New Cluster Compounds , 2010 .

[208]  S. Shore,et al.  Preparation and properties of borate salts. A new synthesis of decaborane(14) , 1967 .

[209]  K. Markides,et al.  Comparison of oligo(ethylene oxide)-substituted polysiloxanes with poly(ethylene glycol) as stationary phases for capillary chromatography , 1988 .

[210]  C. Pittman,et al.  DECHLORINATION OF 4-CHLOROBIPHENYL USING NABH4 AT 120-310 C IN HIGH BOILING INERT SOLVENTS WITH AND WITHOUT LICL , 1997 .

[211]  Howard W. H. Lee,et al.  Solution Synthesis and Characterization of Quantum Confined Ge Nanoparticles , 1999 .

[212]  D. Bergbreiter,et al.  Catalytic reductions of alkyl halides using soluble polyethers and tri-n-butyltin chloride as cocatalysts , 1987 .

[213]  H. Gschwend,et al.  Reaction of n-, sec-, and tert-butyllithium with dimethoxyethane (DME): a correction , 1984 .

[214]  R. Puddephatt,et al.  Chemical Vapor Deposition of Cerium Oxide Using the Precursors [Ce(hfac)3(glyme)] , 2000 .

[215]  J. Mooij,et al.  Structure of alkali biphenyl ion pairs in solution and in the solid state , 1979 .

[216]  W. Henderson,et al.  Tetraglyme−Li+ Cation Solvate Structures: Models for Amorphous Concentrated Liquid and Polymer Electrolytes (II) , 2003 .

[217]  S. Tobishima,et al.  Glyme-based nonaqueous electrolytes for rechargeable lithium cells , 2004 .

[218]  C. Pittman,et al.  Organometallic polymers. XVI. Copolymerization of styrenetricarbonylchromium and the reaction of polystyrene with chromium hexacarbonyl , 1972 .

[219]  G. Pez,et al.  Reactivity of .mu.-(.eta.1:.eta.5-cyclopentadienyl)-tris(.eta.-cyclopentadienyl)dititanium ([.mu.-(.eta.1:.eta.5-C5H4)](.eta.-C5H5)3Ti2) with dinitrogen. Structure of a titanium complex with a triply coordinated dinitrogen ligand , 1982 .

[220]  Anja E.M. Janssen,et al.  Thermodynamically controlled synthesis of β-lactam antibiotics. Equilibrium concentrations and side-chain properties , 1999 .

[221]  M. Siekierski,et al.  NMR studies of equilibriums in electrolytes: Ionic pairing in glymes , 2010 .

[222]  S. Murakami,et al.  Thermodynamic properties of 2,5,8-trioxanonane + n-octane mixture at 298.15 K , 1991 .

[223]  H. Ohno,et al.  Redox reaction of poly(ethylene oxide)-modified hemoglobin in poly(ethylene oxide) oligomers at 120 degrees C. , 1994, Bioconjugate chemistry.

[224]  Teresa Treszczanowicz,et al.  (Liquid + liquid) equilibria in (a dimethyl ether of a polyethene glycol + an n-alkane) , 1993 .

[225]  T. Aminabhavi,et al.  Densities, Viscosities, and Refractive Indices of Bis(2-methoxyethyl) Ether + Cyclohexane or + 1,2,3,4-Tetrahydronaphthalene and of 2-Ethoxyethanol + Propan-1-ol, + Propan-2-ol, or + Butan-1-ol , 1995 .

[226]  Masato Yoshida,et al.  Favorable combination of positive and negative electrode materials with glyme–Li salt complex electrolytes in lithium ion batteries , 2011 .

[227]  P. Spencer New toxicity data for the propylene glycol ethers - a commitment to public health and safety. , 2005, Toxicology letters.

[228]  F. Alloin,et al.  Electrochemical properties of ether-based electrolytes for lithium/sulfur rechargeable batteries , 2013 .

[229]  W. Henderson Crystallization Kinetics of Glyme-LiX and PEO-LiX Polymer Electrolytes , 2007 .

[230]  A. Mau,et al.  Ionochromism in a light-emitting electrochemical cell with low response time based on an ionic conductive poly-phenylene vinylene , 1999 .

[231]  K. Takei,et al.  Charge/discharge performances of glyme–lithium salt equimolar complex electrolyte for lithium secondary batteries , 2013 .

[232]  M. Wentland,et al.  Thermal rearrangement of cyclopropyl imines. IV. Total synthesis of dl-mesembrine. , 1968, Journal of the American Chemical Society.

[233]  Kathleen N. Smith,et al.  Results of testing fifteen glycol ethers in a short-term in vivo reproductive toxicity assay. , 1984, Environmental health perspectives.

[234]  Frank A. P. C. Gobas,et al.  A review of bioconcentration factor (BCF) and bioaccumulation factor (BAF) assessments for organic chemicals in aquatic organisms , 2006 .

[235]  L. Krause,et al.  Bis(trifluoromethyl)cadmium·glyme (glyme = dimethoxyethane), a new, powerful fluoroalkylating agent and low-temperature source of difluorocarbene , 1980 .

[236]  Hajime Miyashiro,et al.  Physicochemical and Electrochemical Properties of Glyme-LiN(SO2F)2 Complex for Safe Lithium-ion Secondary Battery Electrolyte , 2011 .

[237]  E. Akiba,et al.  1H, 7Li, and 19F nuclear magnetic resonance and ionic conductivity studies for liquid electrolytes composed of glymes and polyetheneglycol dimethyl ethers of CH3O(CH2CH2O)nCH3 (n=3–50) doped with LiN(SO2CF3)2 , 2002 .

[238]  R. Rieke,et al.  Metallic nickel-mediated synthesis of ketones by the reaction of benzylic, allylic, vinylic, and pentafluorophenyl halides with acid halides , 1985 .

[239]  J. Jagur-grodzinski,et al.  Structure and reactivities of ion pairs and free ions studied by electron spin resonance spectroscopy. Effect of coordination with tetraglyme , 1969 .

[240]  G. Stork,et al.  Isolation of ketone enolates as trialkylsilyl ethers , 1968 .

[241]  L. Miller,et al.  Electron-transfer reduction of dibenzonorcaradiene. Orbital symmetry considerations in an ion radical reaction , 1969 .

[242]  W. Xu,et al.  Affinities of crown ethers, glymes, and polyamines for alkali picrates in toluene: application of polymer-supported linear polyethers , 1984 .

[243]  T. Macdonald,et al.  Synthesis of d,l-muscone from cyclododecanone , 1975 .

[244]  M. Ratner,et al.  Molecular dynamics simulations of ion clustering and conductivity in NaI/ether solutions. II. Effect of ion concentration , 1995 .

[245]  D. Seeley,et al.  Catalytic fixation of molecular nitrogen by electrolytic and chemical reduction , 1969 .

[246]  Pedro J. Bernal,et al.  Apparent Molar Volumes and Adiabatic Compressibilities of Crown Ethers and Glymes in Aqueous Solutions at Various Temperatures , 2000 .

[247]  R. Sheldon,et al.  Cross-linked enzyme aggregates: a simple and effective method for the immobilization of penicillin acylase. , 2000, Organic letters.

[248]  R. Rieke,et al.  Preparation of highly reactive metal powders: preparation, characterization, and chemistry of iron, cobalt, nickel, palladium, and platinum microparticles , 1983 .

[249]  P. Stang,et al.  UNSATURATED CARBENES FROM PRIMARY VINYL TRIFLATES PART 4, SIMPLE ALKYL METHYLENECYCLOPROPENES VIA ADDITION OF UNSATURATED CARBENES TO ALKYNES , 1975 .

[250]  M. Siekierski,et al.  Estimation of ion pair formation constants of lithium salts in mixtures of glymes and 1,4-dioxane , 2007 .

[251]  D. Seung,et al.  Cycling a Sulfur Electrode in Electrolytes Based on Sulfolane and Linear Ethers (Glymes) in an LiCF3SO3 Solution , 2002 .

[252]  P. Bruce,et al.  Ionic conductivity in the solid glyme complexes [CH3O(CH2CH2O)(n)CH3]:LiAsF6 (n = 3,4). , 2007, Journal of the American Chemical Society.

[253]  A. Mckillop,et al.  Thallium in organic synthesis. XXXVIII. Oxidation of chalcones, deoxybenzoins, and benzoins with thallium(III) nitrate (TTN) , 1973 .

[254]  R. Jerome,et al.  Anionic Polymerization of Acrylic Monomers. 14. Carbon-13 and Lithium-7 NMR Characterization of the Complexation of Methyl .alpha.-Lithioisobutyrate with Various Lithium Cation-Binding Ligands in Tetrahydrofuran , 1994 .

[255]  Y. Inoue,et al.  Enthalpy–entropy compensation in complexation of cations with crown ethers and related ligands , 1985 .

[256]  J. S. Beck,et al.  Synthesis, Properties, and Ceramic Conversion Reactions of Polyborazylene. A High-Yield Polymeric Precursor to Boron Nitride , 1995 .

[257]  M. Ratner,et al.  Ion clustering in molecular dynamics simulations of sodium iodide solutions , 1995 .

[258]  P. Kebarle,et al.  Binding energies and stabilities of potassium ion complexes with ethylene diamine and dimethoxyethane (glyme) from measurements of the complexing equilibria in the gas phase , 1976 .

[259]  J. Vittal,et al.  Yttrium β-diketonate complexes with triglyme: ionic and neutral isomers and outer-sphere co-ordination of triglyme† , 1998 .

[260]  S. Daniele,et al.  Synthesis, characterisation and grafting onto silica of alkoxide-triflate lanthanum complexes. Molecular structure of La(OC6H3-2,6-Me2)2(η1-O3SCF3)(tetraglyme) , 2003 .

[261]  Pascual Pérez,et al.  Green solvents from glycerol. Synthesis and physico-chemical properties of alkyl glycerol ethers , 2010 .

[262]  T. Kitagawa,et al.  Raman Spectroscopic Observations of Anomalous Conformational Behavior of Short Poly(oxyethylene) Chains in Water , 1995 .

[263]  M. Cocchi,et al.  The 2-Methoxyethanol + 1,2-Dimethoxyethane + Water Ternary System. Static Relative Permittivities from −10 To +80°C , 2001 .

[264]  H. Matsuura,et al.  Conformational behaviour of short poly(oxyethylene) compounds in formamide: a Raman spectroscopic study , 1996 .

[265]  L. Krause,et al.  Trifluoromethyl Group 2B compounds: formation of mono- and bis-(trifluoromethyl)–platinum, –palladium, and –nickel trialkylphosphine complexes from the reaction of (CF3)2Cd·glyme [glyme =(CH2OMe)2] with the diligand metal dihalides , 1981 .

[266]  G. Collins,et al.  Effect of chain length on the glyme-separated ion-pair formation in bolaform salts of α,ω-(9-fluorenyl)polymethylenes , 1978 .

[267]  S. Seki,et al.  Oxidative-stability enhancement and charge transport mechanism in glyme-lithium salt equimolar complexes. , 2011, Journal of the American Chemical Society.

[268]  V. Aviyente,et al.  Modeling Proton-Bound Methanol, Ammonia, and Amine Complexes of 12-Crown-4-Ether and Dimethoxyethane (“Glyme”) Using Density Functional Theory , 1998 .

[269]  S. Rosen,et al.  Preparation, Stability and Use Preformed Solutions of Iodine Isocyanate. , 1966 .

[270]  R. Manderville,et al.  Inversion of kinetic and thermodynamic preferences in Meisenheimer complex formation : regioselectivity in the reaction of 2,4,6-trimethylphenoxide ion with 2,4,6-trinitroanisole and the importance of stereoelectronic factors , 1993 .

[271]  B. D. Hardin,et al.  Relative potency of four ethylene glycol ethers for induction of paw malformations in the CD-1 mouse. , 1987, Teratology.

[272]  J. Adcock,et al.  Synthesis of the fluorinated ethers, "perfluoroglyme" and "perfluorodiglyme" by direct fluorination , 1973 .

[273]  R. Manderville,et al.  Regioselectivity and stereoelectronic factors in the reactions of aryloxide nucleophiles with 4-nitrobenzofuroxan , 1993 .

[274]  W. Tyrra,et al.  Tetramethylammonium trifluoromethyltellurate(0), [NMe4]TeCF3, synthesis, characterisation and properties , 2004 .

[275]  J. Schomaker,et al.  Arylation of halogenated pyrimidines via a Suzuki coupling reaction. , 2001, The Journal of organic chemistry.

[276]  L. Lepori,et al.  Volumes of mixing of ethers with tetrachloromethane at 298.15 K , 1991 .

[277]  S. Scheiner,et al.  COMPLEXING OF THE AMMONIUM ION BY POLYETHERS. COMPARATIVE COMPLEXING THERMOCHEMISTRY OF AMMONIUM, HYDRONIUM, AND ALKALI CATIONS , 1996 .

[278]  B. Hoge,et al.  A new synthesis of trifluoromethanethiolates—characterization and properties of tetramethylammonium, cesium and di(benzo-15-crown-5)cesium trifluoromethanethiolates , 2003 .

[279]  J. Morrison,et al.  Preparation and properties of (.eta.5-C5H5)Co(CO)(CF3)2. The reaction of (CF3)2Cd.cntdot.glyme with CpCo(CO)I2 , 1986 .

[280]  A. M. Grotens,et al.  Viscosity behavior of solutions of sodium tetraphenylboron and its glyme complexes in ethereal solvents , 1973 .

[281]  I. Kolthoff,et al.  X-ray crystal structure of the 1∶2∶2 pentaethyleneglycol dimethyl ether(pentaglyme)∶dichloropicric acid∶water complex. Infrared studies of the 1∶2∶2 complexes with tri-, tetra-, and pentaglyme , 1993 .

[282]  K. P. Lee,et al.  Comparative testicular toxicity of bis(2-methoxyethyl) ether and 2-methoxyethanol in rats. , 1989, Toxicology.

[283]  J. Daridon,et al.  Thermophysical Properties of Two Poly(alkylene glycol) Derivative Lubricants from High Pressure Acoustic Measurements , 2003 .

[284]  J. Kennedy,et al.  Phosphacarborane chemistry. New cluster isomers in the eleven-vertex nido-phosphadicarbaborane series: synthesis of the nido phosphadicarbaboranes 7,8,11-PC2B8H11, [7,8,11-PC2B8H10]- and 7-Ph-7,8,10-PC2B8H10 , 2000 .

[285]  D. Seung,et al.  Cycling a Sulfur Electrode: Effect of Physicochemical Properties of Electrolyte Systems , 2003 .

[286]  P. Tontiwachwuthikul,et al.  Solubilities of Carbon Dioxide in Polyethylene Glycol Ethers , 2008 .

[287]  J. Shapley,et al.  Direct synthesis and interconversion of large rhenium carbonyl clusters , 1988 .

[288]  William S. Bradshaw,et al.  Perinatal toxicity of ethylene glycol dimethyl ether in the rat. , 1991, Reproductive toxicology.

[289]  M. Hursthouse,et al.  Effect of Polyether Ligands on Stabilities and Mass Transport Properties of a Series of Gadolinium(III) .beta.-Diketonate Complexes , 1995 .

[290]  J. Smid,et al.  Contact and solvent-separated ion pairs of carbanions. IV. Specific solvation of alkali ions by polyglycol dimethyl ethers , 1967 .

[291]  A. Coronas,et al.  Experimental and predicted excess enthalpies of the working pairs (methanol or trifluoroethanol + polyglycol ethers) for absorption cycles , 1997 .

[292]  Alexandre Varnek,et al.  Assessment of the Macrocyclic Effect for the Complexation of Crown-Ethers with Alkali Cations Using the Substructural Molecular Fragments Method , 2002, J. Chem. Inf. Comput. Sci..

[293]  Robin D. Rogers,et al.  Polyethylene glycol and solutions of polyethylene glycol as green reaction media , 2005 .

[294]  W. Tyrra,et al.  Tris(trifluoromethyl)tellurate(II), [Te(CF3)3]−, the dimeric bis(trifluoromethyl)chlorotellurate(II), [(CF3)2TeCl]22−, and bis(trifluoromethyl)iodate(I), [I(CF3)2]−: the first hypervalent alkyl [10-Te-3] and [12-Te-4] species and a novel [10-I-2] compound , 2001 .

[295]  W. Henderson,et al.  Li+ cation coordination in [Li2(CF3SO3)2(diglyme)] and [Li3(C2F3O2)3(diglyme)]. , 2002, Acta crystallographica. Section C, Crystal structure communications.

[296]  J. Morrison,et al.  Synthesis of bis(trifluoromethyl)phenylthallium and bis(trifluoromethyl)thallium acetate. Oxidative trifluoromethylation with bis(trifluoromethyl)thallium(III) compounds , 1989 .

[297]  R. Rasmussen,et al.  Preparation and Favorskii reaction of equatorial and axial 2-bromobenzo[6,7]bicyclo[3.2.1]oct-6-en-3-one , 1975 .

[298]  S. P. Gejji,et al.  Electronic structure and normal vibrations of CH3(OCH2CH2)nOCH3-M+-CF3SO3- (n = 2-4, M = Li, Na, and K). , 2006, The journal of physical chemistry. A.

[299]  G. Żukowska,et al.  Influence of macromolecular additives on transport properties of lithium organic electrolytes , 2006 .

[300]  Ronald L. Bruening,et al.  Thermodynamic and kinetic data for macrocycle interactions with cations and anions , 1991 .

[301]  Y. Sakka,et al.  Controlled organic/inorganic interface leading to the size-tunable luminescence from Si nanoparticles , 2010 .

[302]  Ian D. Williams,et al.  Synthesis, isomer separation, and metal complexation studies of aza- and oxaphosphands, a class of hard/soft dinucleating phosphine macrocycles , 1990 .

[303]  Ian D. Williams,et al.  Aza- and oxaphosphands, a new class of hard/soft binucleating phosphine macrocycles , 1986 .

[304]  O. S. Tee,et al.  Hydrolysis of p-nitrophenyl alkanoates in aqueous organic solvent mixtures. The dispersal of aggregates and the uncoiling of n-alkyl chains , 1988 .

[305]  O. Engkvist,et al.  A Monte Carlo simulation study of the temperature dependence for the conformation distribution of 1,2-dimethoxyethane in water , 1997 .

[306]  C. Winter,et al.  Synthesis and characterization of calcium complexes containing eta 2-pyrazolato ligands. , 2000, Inorganic chemistry.

[307]  G. Ledoux,et al.  Novel heterometal-organic complexes as first single source precursors for up-converting NaY(Ln)F4 (Ln = Yb, Er, Tm) nanomaterials. , 2012, Dalton transactions.

[308]  M. Szwarc,et al.  Ion pairs. Isomerization of ion pairs possessing a solvated agent on their periphery into the agent-separated pairs , 1967 .

[309]  S. Joo,et al.  Catalytic effect of laser ablated Ni nanoparticles in the oxidative addition reaction for a coupling reagent of benzylchloride and bromoacetonitrile , 2005 .

[310]  W. T. Reichle Reaction of haloaryl sulfones with alkali phenoxides. Effects of polyglyme solvents and other variables , 1972 .

[311]  R. Murray,et al.  Solvent Dynamics Effects on Heterogeneous Electron Transfer Rate Constants of Cobalt Tris(bipyridine) , 1996 .