Viscosity behavior of solutions of sodium tetraphenylboron and its glyme complexes in ethereal solvents

Smid, Johannes; Grotens, A. M.

doi:10.1021/j100639a003

Cited by 18 publications

(3 citation statements)

References 11 publications

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“…Smid and Grotens 128 reported the crystalline 1:l complexes of NaBPh 4 with glyme-5, glyme-6 and glyme-7, as well as a 2:l complex with glyme-4. de Boer et al 129 studied the alkali biphenyl (NaBp, KBp and RbBp) in triglyme or tetraglyme solutions by NMR and the crystal structures of NaBp·(2 triglyme), KBp·(2 tetraglyme) and RbBp·(2 tetraglyme) by X-ray diffraction; these crystals consist of solvent-separated ion pairs in the solid state.…”

Section: Physicochemical and Metal Complexing Properties Of Glymesmentioning

confidence: 99%

Glymes as versatile solvents for chemical reactions and processes: from the laboratory to industry

2014

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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.

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Section: Physicochemical and Metal Complexing Properties Of Glymesmentioning

confidence: 99%

Glymes as versatile solvents for chemical reactions and processes: from the laboratory to industry

2014

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“…This may prevent the formation of the crystal. It is noteworthy that Smid and Grotens (17) were able to make single crystal of Na-tetraphenylborate (NaBPh) of composition NaBPh.2Tg. Since the crystal structure is yet unknown, it is not certain if all oxygen atoms are coordinated to the sodium ion.…”

Section: Broadening Of the Alkali Resonance Linesmentioning

confidence: 99%

Structure of alkali biphenyl ion pairs in solution and in the solid state

Boer¹,

Klaassen²,

Mooij³

et al. 1979

Pure and Applied Chemistry

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NMR experiments on sodium biphenyl (NaBp), potassium biphenyl (KBp) and ribidium biphenyl (RbBp), dissolved in various solvents are summarized with emphasis on the structural information which can be obtained from such experiments. The crystal structures of NaBp.2Tg (Tg = triglyme), KBp.2Ttg and RbBp.2Ttg (Ttg tetraglyme) are discussed, in relation to the NMR results obtained for these systems in solution. In the solid state these crystals may be considered to be built up of solvent separated ion pairs. Magnetic experiments are reported for single crystals of the three systems. Susceptibility measurements revealed a ferromagnetic coupling in NaBp.2Tg and KBp.2Ttg and an antiferromagnetic coupling in RbBp.2Ttg. All crystals exhibit an exchange narrowed ESR line, with an orientation dependent linewidth. From the resonance positions the molecular g tensor of the biphenyl anion could be derived. The orientation dependent linewidth is due to dipolar interactions between the spins. A quantitative explanation of it could not be given at present.

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“…While glyme 5 (the number following the glyme refers to the number of oxygen atoms, i.e., tetraethylene glycol dimethyl ether) or glyme 6 form 1:1 complexes with Na+ in THF,14 glyme 3 and glyme 4 can also form stable 2:1 complexes. 16,19 With potassium salts 2:1 glyme-cation complexes are found for glyme 4 and glyme 5, while glyme 6 and glyme 7 form 1:1 complexes. 14 The number of sites to which Na+ binds to a glyme is probably not more than six, and higher Ke values for this cation with glymes of more than six oxygen atoms are basically due to a statistical factor resulting from the increased number of available binding sites.14 However, K+ may have as many as ten oxygen atoms in its solvation shell (e.g., dibenzo-30-crown-10 has all of its ten oxygen atoms wrapped around the K+ ion and is a very effective complexing agent for this cation11).…”

Section: Resultsmentioning

confidence: 97%