Protic solvent

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In chemistry, a protic solvent is a solvent that has a hydrogen atom bound to an oxygen (as in a hydroxyl group −OH), a nitrogen (as in an amine group −NH2 or −NH−), or fluoride (as in hydrogen fluoride). In general terms, any solvent that contains a labile H+ is called a protic solvent. The molecules of such solvents readily donate protons (H+) 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. [1] [2]

Methods for purification of common solvents are available [3]

Solvent Chemical formula Boiling point Dielectric constant Density Dipole moment (D)
Polar protic solvents
formic acid HCO2H101 °C581.21 g/mL1.41 D
n-butanol CH3CH2CH2CH2OH118 °C180.810 g/mL1.63 D
isopropanol (IPA)(CH3)2CH(OH)82 °C180.785 g/mL1.66 D
nitromethane [note 2] CH3NO2101°C35.871.1371 g/mL3.56 D
ethanol (EtOH)CH3CH2OH79 °C24.550.789 g/mL1.69 D
methanol (MeOH)CH3OH65 °C330.791 g/mL1.70 D
Acetic acid (AcOH)CH3CO2H118 °C6.21.049 g/mL1.74 D
Water H2O100 °C801.000 g/mL1.85 D

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An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen ion, H+), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid.

<span class="mw-page-title-main">Acid–base reaction</span> Chemical reaction between an acid and a base

In chemistry, an acid–base reaction is a chemical reaction that occurs between an acid and a base. It can be used to determine pH via titration. Several theoretical frameworks provide alternative conceptions of the reaction mechanisms and their application in solving related problems; these are called the acid–base theories, for example, Brønsted–Lowry acid–base theory.

<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.

<span class="mw-page-title-main">Solvation</span> Association of molecules of a solvent with molecules or ions of a solute

Solvation describes the interaction of a solvent with dissolved molecules. Both ionized and uncharged molecules interact strongly with a solvent, and the strength and nature of this interaction influence many properties of the solute, including solubility, reactivity, and color, as well as influencing the properties of the solvent such as its viscosity and density. 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. The surrounded solute particles then move away from the solid solute and out into the solution. Ions are surrounded by a concentric shell of solvent. Solvation is the process of reorganizing solvent and solute molecules into solvation complexes and involves bond formation, hydrogen bonding, and van der Waals forces. Solvation of a solute by water is called hydration.

In chemistry, an acid dissociation constant is a quantitative measure of the strength of an acid in solution. It is the equilibrium constant for a chemical reaction

<span class="mw-page-title-main">Hydride</span> Molecule with a hydrogen bound to a more electropositive element or group

In chemistry, a hydride is formally the anion of hydrogen (H), a hydrogen atom with two electrons. The term is applied loosely. At one extreme, all compounds containing covalently bound H atoms are called hydrides: water (H2O) is a hydride of oxygen, ammonia is a hydride of nitrogen, etc. For inorganic chemists, hydrides refer to compounds and ions in which hydrogen is covalently attached to a less electronegative element. In such cases, the H centre has nucleophilic character, which contrasts with the protic character of acids. The hydride anion is very rarely observed.

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

Bimolecular nucleophilic substitution (SN2) is a type of reaction mechanism that is common in organic chemistry. In the SN2 reaction, a strong nucleophile forms a new bond to an sp3-hybridised carbon via a backside attack, all while the leaving group detaches from the reaction center in a concerted fashion.

The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction theory which was first developed by Johannes Nicolaus Brønsted and Thomas Martin Lowry independently in 1923. The basic concept of this theory is that when an acid and a base react with each other, the acid forms its conjugate base, and the base forms its conjugate acid by exchange of a proton (the hydrogen cation, or H+). This theory generalises the Arrhenius theory.

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

Fluorosulfuric acid (IUPAC name: sulfurofluoridic acid) is the inorganic compound with the chemical formula HSO3F. It is one of the strongest acids commercially available. It is a tetrahedral molecule and is closely related to sulfuric acid, H2SO4, substituting a fluorine atom for one of the hydroxyl groups. It is a colourless liquid, although commercial samples are often yellow.

An inorganic nonaqueous solvent is a solvent other than water, that is not an organic compound. These solvents are used in chemical research and industry for reactions that cannot occur in aqueous solutions or require a special environment. Inorganic nonaqueous solvents can be classified into two groups, protic solvents and aprotic solvents. Early studies on inorganic nonaqueous solvents evaluated ammonia, hydrogen fluoride, sulfuric acid, as well as more specialized solvents, hydrazine, and selenium oxychloride.

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

Fluoroantimonic acid is a mixture of hydrogen fluoride and antimony penta­fluoride, containing various cations and anions. This mixture is a superacid that, in terms of corrosiveness, is trillions of times stronger than 100% sulfuric acid in terms of its protonating ability measured by Hammett function. It even protonates some hydro­carbons to afford pentacoordinate carbo­cations. Like its precursor hydrogen fluoride, it attacks glass, but can be stored in containers lined with PTFE (Teflon) or PFA.

<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">Fluoroboric acid</span> Chemical compound

Fluoroboric acid or tetrafluoroboric acid is an inorganic compound with the simplified chemical formula H+[BF4]. Unlike other strong acids like H2SO4 or HClO4, the pure tetrafluoroboric acid does not exist. The term "fluoroboric acid" refers to a range of chemical compounds, depending on the solvent. The H+ in the simplified formula of fluoroboric acid represents the solvated proton. The solvent can be any suitable Lewis base. For instance, if the solvent is water, fluoroboric acid can be represented by the formula [H3O]+[BF4], although more realistically, several water molecules solvate the proton: [H(H2O)n]+[BF4]. The ethyl ether solvate is also commercially available, where the fluoroboric acid can be represented by the formula [H( 2O)n]+[BF4], where n is most likely 2.

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

Molybdenum hexafluoride, also molybdenum(VI) fluoride, is the inorganic compound with the formula MoF6. It is the highest fluoride of molybdenum. It is a colourless solid and melts just below room temperature and boils in 34 °C. It is one of the seventeen known binary hexafluorides.

Electrochemical fluorination (ECF), or electrofluorination, is a foundational organofluorine chemistry method for the preparation of fluorocarbon-based organofluorine compounds. The general approach represents an application of electrosynthesis. The fluorinated chemical compounds produced by ECF are useful because of their distinctive solvation properties and the relative inertness of carbon–fluorine bonds. Two ECF synthesis routes are commercialized and commonly applied: the Simons process and the Phillips Petroleum process. It is also possible to electrofluorinate in various organic media. Prior to the development of these methods, fluorination with fluorine, a dangerous oxidizing agent, was a dangerous and wasteful process. ECF can be cost-effective, but it may also result in low yields.

Acid strength is the tendency of an acid, symbolised by the chemical formula , to dissociate into a proton, , and an anion, . The dissociation of a strong acid in solution is effectively complete, except in its most concentrated solutions.

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.