Acid

Acids and bases:

• Acid-base extraction
• Acid-base reaction
• Acid-base physiology
• Acid-base homeostasis
• Dissociation constant
• Acidity function
• Buffer solutions
• pH
• Proton affinity
• Self-ionization of water
• Acids:
  • Lewis acids
  • Mineral acids
  • Organic acids
  • Strong acids
  • Superacids
  • Weak acids
• Bases:
  • Lewis bases
  • Organic bases
  • Strong bases
  • Superbases
  • Non-nucleophilic bases
  • Weak bases

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

An acid (often represented by the generic formula HA [H⁺A^-]) is traditionally considered any chemical compound that, when dissolved in water, gives a solution with a hydrogen ion activity greater than in pure water, i.e. a pH less than 7.0. That approximates the modern definition of Johannes Nicolaus Brønsted and Martin Lowry, who independently defined an acid as a compound which donates a hydrogen ion (H⁺) to another compound (called a base). Common examples include acetic acid (in vinegar) and sulfuric acid (used in car batteries). Acid/base systems are different from redox reactions in that there is no change in oxidation state.

Definitions

Main article: acid-base reaction theories

The word "acid" comes from the Latin acidus meaning "sour," but in chemistry the term acid has a more specific meaning. There are four common ways to define an acid:

• Arrhenius: According to this definition developed by the Swedish chemist Svante Arrhenius, an acid is a substance that increases the concentration of hydrogen ions (H⁺), which are carried as hydronium ions (H₃O⁺) when dissolved in water, while bases are substances that increase the concentration of hydroxide ions (OH^-). This definition limits acids and bases to substances that can dissolve in water. Around 1800, many French chemists, including Antoine Lavoisier, incorrectly believed that all acids contained oxygen. Indeed the modern German word for oxygen is Sauerstoff (lit. sour substance), as is the Afrikaans word for oxygen suurstof, with the same meaning. English chemists, including Sir Humphry Davy at the same time believed all acids contained hydrogen. Arrhenius used this belief to develop this definition of acid.
• Brønsted-Lowry: According to this definition, an acid is a proton (hydrogen nucleus) donor and a base is a proton acceptor. The acid is said to be dissociated after the proton is donated. An acid and the corresponding base are referred to as conjugate acid-base pairs. Brønsted and Lowry independently formulated this definition, which includes water-insoluble substances not in the Arrhenius definition.
• solvent-system definition: According to this definition, an acid is a substance that, when dissolved in an autodissociating solvent, increases the concentration of the solvonium cations, such as H₃O⁺ in water, NH₄⁺ in liquid ammonia, NO⁺ in liquid N₂O₄, SbCl₂⁺ in SbCl₃, etc. Base is defined as the substance that increases the concentration of the solvate anions, respectively OH^-, NH₂^-, NO₃^-, or SbCl₄^-. This definition extends acid-base reactions to nonaqueous systems and even some aprotic systems, where no hydrogen nuclei are involved in the reactions. This definition is not absolute, a compound acting as acid in one solvent may act as a base in another.
• Lewis: According to this definition developed by Gilbert N. Lewis, an acid is an electron-pair acceptor and a base is an electron-pair donor. (These are frequently referred to as "Lewis acids" and "Lewis bases," and are electrophiles and nucleophiles, respectively, in organic chemistry; Lewis bases are also ligands in coordination chemistry.) Lewis acids include substances with no transferable protons (ie H⁺ hydrogen ions), such as iron(III) chloride, and hence the Lewis definition of an acid has wider application than the Brønsted-Lowry definition. In fact, the term Lewis acid is often used to exclude protic (Brønsted-Lowry) acids. The Lewis definition can also be explained with molecular orbital theory. In general, an acid can receive an electron pair in its lowest unoccupied orbital (LUMO) from the highest occupied orbital (HOMO) of a base. That is, the HOMO from the base and the LUMO from the acid combine to a bonding molecular orbital.

Although not the most general theory, the Brønsted-Lowry definition is the most widely used definition. The strength of an acid may be understood by this definition by the stability of hydronium and the solvated conjugate base upon dissociation. Increasing or decreasing stability of the conjugate base will increase or decrease the acidity of a compound. This concept of acidity is used frequently for organic acids such as carboxylic acid. The molecular orbital description, where the unfilled proton orbital overlaps with a lone pair, is connected to the Lewis definition.

Properties

Bronsted-Lowry acids:

• Are generally sour in taste
• Strong or concentrated acids often produce a stinging feeling on mucous membranes
• React to indicators as follows: turn blue litmus and methyl orange red, do not change the color of phenolphthalein
• Will react with metals to produce a metal salt and hydrogen
• Will react with metal carbonates to produce water, CO₂ and a salt
• Will react with a base to produce a salt and water
• Will react with a metal oxide to produce water and a salt
• Will conduct electricity, depending on the degree of dissociation
• Will produce solvonium ions, such as hydronium (H₃O⁺) ions in water
• Will denature proteins

Strong acids and many concentrated acids are dangerous, causing severe burns for even minor contact. Acids are corrosive. Generally, acid burns are treated by rinsing the affected area abundantly with running water (15 minutes) and followed up with immediate medical attention. In the case of highly concentrated acids, the acid should first be wiped off as much as possible, otherwise the exothermic mixing of the acid and the water could cause severe thermal burns. Acids may also be dangerous for reasons not related to their acidity, see an appropriate MSDS for more detailed information.

Nomenclature

In the classical naming system, acids are named according to their anions. That ionic suffix is dropped and replaced with a new suffix (and sometimes prefix), according to the table below. For example, HCl has chloride as its anion, so the -ide suffix makes it take the form hydrochloric acid. In the IUPAC naming system, "aqueous" is simply added to the name of the ionic compound. Thus, for hydrogen chloride, the IUPAC name would be aqueous hydrogen chloride.

Classical naming system:

Anion Prefix	Anion Suffix	Acid Prefix	Acid Suffix	Example
per	ate	per	ic acid	perchloric acid (HClO4)
	ate		ic acid	chloric acid (HClO3)
	ite		ous acid	chlorous acid (HClO2)
hypo	ite	hypo	ous acid	hypochlorous acid (HClO)
	ide	hydro	ic acid	hydrochloric acid (HCl)

Chemical characteristics

In water the following equilibrium occurs between a weak acid (HA) and water, which acts as a base:

HA(aq) + H₂O Template:Unicode H₃O⁺(aq) + A^-(aq)

The acidity constant (or acid dissociation constant) is the equilibrium constant for the reaction of HA with water:

<math>K_a = {[\mbox{H}_3\mbox{O}^+]\cdot[\mbox{A}^-] \over [\mbox{HA}]}</math>

Strong acids have large K_a values (i.e. the reaction equilibrium lies far to the right; the acid is almost completely dissociated to H₃O⁺ and A^-). Strong acids include the heavier hydrohalic acids: hydrochloric acid (HCl), hydrobromic acid (HBr), and hydroiodic acid (HI). (However, hydrofluoric acid, HF, is relatively weak.) For example, the K_a value for hydrochloric acid (HCl) is 10⁷.

Weak acids have small K_a values (i.e. at equilibrium significant amounts of HA and A⁻ exist together in solution; modest levels of H₃O⁺ are present; the acid is only partially dissociated). For example, the K_a value for acetic acid is 1.8 x 10^-5. Most organic acids are weak acids. Oxoacids, which tend to contain central atoms in high oxidation states surrounded by oxygen may be quite strong or weak. Nitric acid, sulfuric acid, and perchloric acid are all strong acids, whereas nitrous acid, sulfurous acid and hypochlorous acid are all weak.

Note on terms used:

• The terms "hydrogen ion" and "proton" are used interchangeably; both refer to H⁺.
• In aqueous solution, the water is protonated to form hydronium ion, H₃O⁺(aq). This is often abbreviated as H⁺(aq) even though the symbol is not chemically correct.
• The strength of an acid is measured by its acid dissociation constant (K_a) or equivalently its pK_a (pK_a= - log(K_a)).
• The pH of a solution is a measurement of the concentration of hydronium. This will depend on the concentration and nature of acids and bases in solution.

Polyprotic acids

Polyprotic acids are able to donate more than one proton per acid molecule, in contrast to monoprotic acids that only donate one proton per molecule. Specific types of polyprotic acids have more specific names, such as diprotic acid (two potential protons to donate) and triprotic acid (three potential protons to donate).

A monoprotic acid can undergo one dissociation (sometimes called ionization) as follows and simply has one acid dissociation constant as shown below:

HA(aq) + H₂O(l) Template:Unicode H₃O⁺(aq) + A⁻(aq)         K_a

A diprotic acid (here symbolized by H₂A) can undergo one or two dissociations depending on the pH. Each dissociation has its own dissociation constant, K_a1 and K_a2.

H₂A(aq) + H₂O(l) Template:Unicode H₃O⁺(aq) + HA⁻(aq)       K_a1

HA⁻(aq) + H₂O(l) Template:Unicode H₃O⁺(aq) + A²⁻(aq)       K_a2

The first dissociation constant is typically greater than the second; i.e., K_a1 > K_a2 . For example, sulfuric acid (H₂SO₄) can donate one proton to form the bisulfate anion (HSO₄⁻), for which K_a1 is very large; then it can donate a second proton to form the sulfate anion (SO₄²⁻), wherein the K_a2 is intermediate strength. The large K_a1 for the first dissociation makes sulfuric a strong acid. In a similar manner, the weak unstable carbonic acid (H₂CO₃) can lose one proton to form bicarbonate anion (HCO₃⁻) and lose a second to form carbonate anion (CO₃²⁻). Both K_a values are small, but K_a1 > K_a2 .

A triprotic acid (H₃A) can undergo one, two, or three dissociations and has three dissociation constants, where K_a1 > K_a2 > K_a3 .

H₃A(aq) + H₂O(l) Template:Unicode H₃O⁺(aq) + H₂A⁻(aq)        K_a1

H₂A⁻(aq) + H₂O(l) Template:Unicode H₃O⁺(aq) + HA²⁻(aq)       K_a2

HA²⁻(aq) + H₂O(l) Template:Unicode H₃O⁺(aq) + A³⁻(aq)         K_a3

An inorganic example of a triprotic acid is orthophosphoric acid (H₃PO₄), usually just called phosphoric acid. All three protons can be successively lost to yield H₂PO₄⁻, then HPO₄²⁻, and finally PO₄³⁻ , the orthophosphate ion, usually just called phosphate. An organic example of a triprotic acid is citric acid, which can successively lose three protons to finally form the citrate ion. Even though the positions of the protons on the original molecule may be equivalent, the successive K_a values will differ since it is energetically less favorable to lose a proton if the conjugate base is more negatively charged.

Neutralization

Neutralization is the reaction between an acid and a base, producing a salt and water; for example, hydrochloric acid and sodium hydroxide form sodium chloride and water:

HCl(aq) + NaOH(aq) → H₂O(l) + NaCl(aq)

Neutralization is the basis of titration, where a pH indicator shows equivalence point when the equivalent number of moles of a base have been added to an acid. It is often wrongly assumed that neutralization should result in a solution with pH 7.0, which is only the case with similar acid and base strengths during a reaction.

Neutralization with an base weaker than the acid results in an weakly acidic salt. An example is the weakly acidic ammonium chloride, which is produced from the strong acid hydrogen chloride and the weak base ammonia. Conversely, neutralizing a weak acid with a strong base gives a weakly basic salt, e.g. sodium fluoride from hydrogen fluoride and sodium hydroxide.

Weak acid/weak base equilibria

Main article: Henderson-Hasselbalch equation

In order to lose a proton, it is necessary that the pH of the system rise above the pK_a of the protonated acid. The decreased concentration of H⁺ in that basic solution shifts the equilibrium towards the conjugate base form (the deprotonated form of the acid). In lower-pH (more acidic) solutions, there is a high enough H⁺ concentration in the solution to cause the acid to remain in its protonated form, or to protonate its conjugate base (the deprotonated form).

Solutions of weak acids and salts of their conjugate bases form buffer solutions.

Applications of acids

There are numerous uses for acids. Acids are often used to remove rust and other corrosion from metals in a process known as pickling. They may be used as an electrolyte in a wet cell battery, such as sulfuric acid in a car battery. In humans and many other animals, hydrochloric acid is a part of the gastric acid secreted within the stomach to help hydrolyze proteins and polysaccharides, as well as converting the inactive pro-enzyme, pepsinogen into the enzyme, pepsin. Acids are used as catalysts; for example, sulfuric acid is used in very large quantities in the alkylation process to produce gasoline.

Common acids

• Citric Acid

Mineral acids

• Solutions of hydrogen halides, such as hydrochloric acid (HCl) and hydrobromic acid (HBr)
• Sulfuric acid (H₂SO₄)
• Nitric acid (HNO₃)
• Phosphoric acid (H₃PO₄)
• Chromic acid (H₂CrO₄)

Sulfonic acids

• Methanesulfonic acid (aka mesylic acid) (MeSO₃H)
• Ethanesulfonic acid (aka esylic acid) (EtSO₃H)
• Benzenesulfonic acid (aka besylic acid) (PhSO₃H)
• Toluenesulfonic acid (aka tosylic acid, or (C₆H₄(CH₃)(SO₃H))

Carboxylic acids

• Formic acid
• Acetic acid

References

• Listing of strengths of common acids and bases
• Zumdahl, Chemistry, 4th Edition.

See also

Chemistry

• Acid value
• Acid salt
• Base (chemistry)
• Basic salt
• Binary acid
• Vitriol
• Acid-base extraction

External links

• Science Aid: Acids and Bases Information for High School students
• Curtipot: Acid-Base equilibria diagrams, pH calculation and titration curves simulation and analysis
• A summary of the Properties of Acids for the beginning chemistry student
• The UN ECE Convention on Long-Range Transboundary Air Pollution

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