Polar aprotic solvent

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A polar aprotic solvent is a solvent that lacks an acidic proton and is polar. Such solvents lack hydroxyl and amine groups. In contrast to protic solvents, these solvents do not serve as proton donors in hydrogen bonding, although they can be proton acceptors. Many solvents, including chlorocarbons and hydrocarbons, are classifiable as aprotic, but polar aprotic solvents are of particular interest for their ability to dissolve salts. [1] [2] Methods for purification of common solvents are available. [3]

Solvent Chemical formula Boiling point Dielectric constant Density Dipole moment (D)Comment
Polar aprotic solvents
acetone C3H6O56.05 °C21.830.7845 g/cm32.91reacts with strong acids and bases
acetonitrile CH3CN81.3 - 82.1 °C38.30.776 g/cm33.20reacts with strong acids and bases
dichloromethane CH2Cl239.6 °C9.081.3266 g/cm31.6low boiling point
dimethylformamide (CH3)2NCHO153 °C36.70.95 g/cm33.86reacts with strong bases
dimethylpropyleneurea (CH3)2C4H6N2O246.5 °C36.121.064 g/cm34.23high boiling point
dimethyl sulfoxide (CH3)2SO189 °C46.71.1 g/cm33.96reacts with strong bases, difficult to purify
ethyl acetate C4H8O277.11°C6.020.902 g/cm31.88reacts with strong bases
hexamethylphosphoramide [(CH3)2N]3PO232.5 °C29.61.03 g/cm35.38high boiling point, high toxicity
pyridine C5H5N115 °C13.30.982 g/cm32.22reacts with protic and Lewis acids
sulfolane C4H8SO2286 °C ?1.27 g/cm34.8high boiling point
tetrahydrofuran C4H8O66 °C7.60.887 g/cm31.75polymerizes in presence of strong protic and Lewis acids

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In chemical analysis, chromatography is a laboratory technique for the separation of a mixture into its components. The mixture is dissolved in a fluid solvent called the mobile phase, which carries it through a system on which a material called the stationary phase is fixed. Because the different constituents of the mixture tend to have different affinities for the stationary phase and are retained for different lengths of time depending on their interactions with its surface sites, the constituents travel at different apparent velocities in the mobile fluid, causing them to separate. The separation is based on the differential partitioning between the mobile and the stationary phases. Subtle differences in a compound's partition coefficient result in differential retention on the stationary phase and thus affect the separation.

<span class="mw-page-title-main">Solution (chemistry)</span> Homogeneous mixture of a solute and a solvent

In chemistry, a solution is a special type of homogeneous mixture composed of two or more substances. In such a mixture, a solute is a substance dissolved in another substance, known as a solvent. If the attractive forces between the solvent and solute particles are greater than the attractive forces holding the solute particles together, the solvent particles pull the solute particles apart and surround them. These surrounded solute particles then move away from the solid solute and out into the solution. The mixing process of a solution happens at a scale where the effects of chemical polarity are involved, resulting in interactions that are specific to solvation. The solution usually has the state of the solvent when the solvent is the larger fraction of the mixture, as is commonly the case. One important parameter of a solution is the concentration, which is a measure of the amount of solute in a given amount of solution or solvent. The term "aqueous solution" is used when one of the solvents is water.

<span class="mw-page-title-main">Solvent</span> Substance dissolving a solute resulting in a solution

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules, and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell.

Acetonitrile, often abbreviated MeCN, is the chemical compound with the formula CH3CN and structure H3C−C≡N. This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene. The N≡C−C skeleton is linear with a short C≡N distance of 1.16 Å.

S<sub>N</sub>2 reaction Substitution reaction where bonds are broken and formed simultaneously

The SN2 reaction is a type of reaction mechanism that is common in organic chemistry. In this mechanism, one bond is broken and one bond is formed in a concerted way, i.e., in one step. The name SN2 refers to the Hughes-Ingold symbol of the mechanism: "SN" indicates that the reaction is a nucleophilic substitution, and "2" that it proceeds via a bi-molecular mechanism, which means both the reacting species are involved in the rate-determining step. The other major type of nucleophilic substitution is the SN1, but many other more specialized mechanisms describe substitution reactions.

Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula CH
3
NO
2
. It is the simplest organic nitro compound. It is a polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent. As an intermediate in organic synthesis, it is used widely in the manufacture of pesticides, explosives, fibers, and coatings. Nitromethane is used as a fuel additive in various motorsports and hobbies, e.g. Top Fuel drag racing and miniature internal combustion engines in radio control, control line and free flight model aircraft.

<span class="mw-page-title-main">Lithium diisopropylamide</span> Chemical compound

Lithium diisopropylamide is a chemical compound with the molecular formula LiN(CH 2)2. It is used as a strong base and has been widely utilized due to its good solubility in non-polar organic solvents and non-nucleophilic nature. It is a colorless solid, but is usually generated and observed only in solution. It was first prepared by Hamell and Levine in 1950 along with several other hindered lithium diorganylamides to effect the deprotonation of esters at the α position without attack of the carbonyl group.

The azide-alkyne Huisgen cycloaddition is a 1,3-dipolar cycloaddition between an azide and a terminal or internal alkyne to give a 1,2,3-triazole. Rolf Huisgen was the first to understand the scope of this organic reaction. American chemist Karl Barry Sharpless has referred to this cycloaddition as "the cream of the crop" of click chemistry and "the premier example of a click reaction".

<span class="mw-page-title-main">Carboxylate</span> Chemical group (RCOO); conjugate base of a carboxylic acid

In organic chemistry, a carboxylate is the conjugate base of a carboxylic acid, RCOO. It is an ion with negative charge.

Potassium <i>tert</i>-butoxide Chemical compound

Potassium tert-butoxide (or potassium t-butoxide) is a chemical compound with the formula [(CH3)3COK]n (abbr. KOtBu). This colourless solid is a strong base (pKa of conjugate acid around 17), which is useful in organic synthesis. The compound is often depicted as a salt, and it often behaves as such, but its ionization depends on the solvent.

<span class="mw-page-title-main">2-Pyridone</span> Chemical compound

2-Pyridone is an organic compound with the formula C
5
H
4
NH(O)
. It is a colourless solid. It is well known to form hydrogen bonded dimers and it is also a classic case of a compound that exists as tautomers.

<i>p</i>-Toluenesulfonic acid Chemical compound

p-Toluenesulfonic acid (PTSA, pTSA, or pTsOH) or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H. It is a white extremely hygroscopic solid that is soluble in water, alcohols, and other polar organic solvents. The CH3C6H4SO2 group is known as the tosyl group and is often abbreviated as Ts or Tos. Most often, TsOH refers to the monohydrate, TsOH.H2O.

<span class="mw-page-title-main">Propylene carbonate</span> Chemical compound

Propylene carbonate (often abbreviated PC) is an organic compound with the formula C4H6O3. It is a cyclic carbonate ester derived from propylene glycol. This colorless and odorless liquid is useful as a polar, aprotic solvent. Propylene carbonate is chiral, but is used as the racemic mixture in most contexts.

<span class="mw-page-title-main">Leveling effect</span> Effect of solvents on properties of acids and bases

Leveling effect or solvent leveling refers to the effect of solvent on the properties of acids and bases. The strength of a strong acid is limited ("leveled") by the basicity of the solvent. Similarly the strength of a strong base is leveled by the acidity of the solvent. When a strong acid is dissolved in water, it reacts with it to form hydronium ion (H3O+). An example of this would be the following reaction, where "HA" is the strong acid:

<span class="mw-page-title-main">Phenylmagnesium bromide</span> Chemical compound

Phenylmagnesium bromide, with the simplified formula C
6
H
5
MgBr
, is a magnesium-containing organometallic compound. It is commercially available as a solution in diethyl ether or tetrahydrofuran (THF). Phenylmagnesium bromide is a Grignard reagent. It is often used as a synthetic equivalent for the phenyl "Ph" synthon.

<span class="mw-page-title-main">DMPU</span> Chemical compound

N,N′-Dimethylpropyleneurea (DMPU) is a cyclic urea sometimes used as a polar, aprotic organic solvent. In 1985, Dieter Seebach showed that it is possible to replace the suspected carcinogen hexamethylphosphoramide (HMPA) with DMPU.

In chemistry, solvent effects are the influence of a solvent on chemical reactivity or molecular associations. Solvents can have an effect on solubility, stability and reaction rates and choosing the appropriate solvent allows for thermodynamic and kinetic control over a chemical reaction.

<span class="mw-page-title-main">Tetrolic acid</span> Chemical compound

Tetrolic acid is a short-chain unsaturated carboxylic acid, described by the formula CH3−C≡C−CO2H. Salts and esters of tetrolic acid are known as tetrolates.

In chemistry, a protic solvent is a solvent that has a hydrogen atom bound to an oxygen, a nitrogen, or fluoride. In general terms, any solvent that contains a labile H+ is called a protic solvent. The molecules of such solvents readily donate protons to solutes, often via hydrogen bonding. Water is the most common protic solvent. Conversely, polar aprotic solvents cannot donate protons but still have the ability to dissolve many salts.

<span class="mw-page-title-main">Corey–Nicolaou macrolactonization</span>

Corey–Nicolaou macrolactonization is a named reaction of organic chemistry, for the synthesis of lactones from hydroxy acids, found in 1974. The reaction should take place in a polar aprotic solvent with mild conditions, with the use of 2,2'-Dipyridyldisulfide and triphenylphosphine.

References

  1. Stoye, Dieter (2000). "Solvents". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_437.
  2. John R. Rumble (ed.). "Laboratory Solvent Solvents and Other Liquid Reagents". CRC Handbook of Chemistry and Physics, 102nd Edition (Internet Version 2021). Boca Raton, FL, USA: CRC Press/Taylor & Francis.
  3. W. L. F. Armarego (2017). Purification of Laboratory Chemicals, 8th Edition. Elsevier. ISBN   9780128054567.