Acid

This article is about acids in chemistry. For the drug, substances having the property of an acid are said to be
see Lysergic acid diethylamide. For other uses, see Acid acidic.
(disambiguation).
Common aqueous acids include hydrochloric acid (a so-
Acidity redirects here. For the novelette, see Acidity lution of hydrogen chloride which is found in gastric acid
(novelette).
in the stomach and activates digestive enzymes), acetic
Acidic redirects here. For the band, see Acidic (band). acid (vinegar is a dilute aqueous solution of this liquid),
An acid is a molecule or ion capable of donating a hydron sulfuric acid (used in car batteries), and citric acid (found
in citrus fruits). As these examples show, acids (in the
colloquial sense) can be solutions or pure substances, and
can be derived from acids (in the strict[1] sense) that are
solids, liquids, or gases. Strong acids and some concen-
trated weak acids are corrosive, but there are exceptions
such as carboranes and boric acid.
The second category of acids are Lewis acids, which form
a covalent bond with an electron pair. An example is
boron triuoride (BF3 ), whose boron atom has a vacant
orbital which can form a covalent bond by sharing a lone
pair of electrons on an atom in a base, for example the
nitrogen atom in ammonia (NH3 ). Lewis considered this
as a generalization of the Brnsted denition, so that an
acid is a chemical species that accepts electron pairs ei-
ther directly or by releasing protons (H+ ) into the solu-
tion, which then accept electron pairs. However, hydro-
gen chloride, acetic acid, and most other Brnsted-Lowry
Zinc, a typical metal, reacting with hydrochloric acid, a typical acids cannot form a covalent bond with an electron pair
acid and are therefore not Lewis acids.[4] Conversely, many
Lewis acids are not Arrhenius or Brnsted-Lowry acids.
(proton or hydrogen ion H+ ), or, alternatively, capable of In modern terminology, an acid is implicitly a Brnsted
forming a covalent bond with an electron pair (a Lewis acid and not a Lewis acid, since chemists almost always
acid).[1] refer to a Lewis acid explicitly as a Lewis acid.[4]
The rst category of acids is the proton donors or
Brnsted acids. In the special case of aqueous solutions,
proton donors form the hydronium ion H3 O+ and are 1 Denitions and concepts
known as Arrhenius acids. Brnsted and Lowry gener-
alized the Arrhenius theory to include non-aqueous sol-
vents. A Brnsted or Arrhenius acid usually contains a Main article: Acidbase reaction
hydrogen atom bonded to a chemical structure that is still
energetically favorable after loss of H+ . Modern denitions are concerned with the fundamental
Aqueous Arrhenius acids have characteristic properties chemical reactions common to all acids.
which provide a practical description of an acid.[2] Acids Most acids encountered in everyday life are aqueous so-
form aqueous solutions with a sour taste, can turn blue lutions, or can be dissolved in water, so the Arrhenius and
litmus red, and react with bases and certain metals (like Brnsted-Lowry denitions are the most relevant.
calcium) to form salts. The word acid is derived from the
Latin acidus/acre meaning sour.[3] An aqueous solution The Brnsted-Lowry denition is the most widely used
of an acid has a pH less than 7 and is colloquially also denition; unless otherwise specied, acid-base reactions
+
referred to as 'acid' (as in 'dissolved in acid'), while the are assumed to involve the transfer of a proton (H ) from
strict denition[1] refers only to the solute. A lower pH an acid to a base.
means a higher acidity, and thus a higher concentration Hydronium ions are acids according to all three deni-
of positive hydrogen ions in the solution. Chemicals or tions. Interestingly, although alcohols and amines can be

1
2 1 DEFINITIONS AND CONCEPTS

Brnsted-Lowry acids, they can also function as Lewis the negative logarithm of the concentration of hydronium
bases due to the lone pairs of electrons on their oxygen ions, acidic solutions thus have a pH of less than 7.
and nitrogen atoms.

1.2 BrnstedLowry acids

1.1 Arrhenius acids
Main article: BrnstedLowry acidbase theory
While the Arrhenius concept is useful for describing

Acetic acid, a weak acid, donates a proton (hydrogen ion, high-

lighted in green) to water in an equilibrium reaction to give the
acetate ion and the hydronium ion. Red: oxygen, black: carbon,
white: hydrogen.

many reactions, it is also quite limited in its scope. In

1923 chemists Johannes Nicolaus Brnsted and Thomas
Martin Lowry independently recognized that acid-base
reactions involve the transfer of a proton. A Brnsted-
Lowry acid (or simply Brnsted acid) is a species that
donates a proton to a Brnsted-Lowry base.[5] Brnsted-
Lowry acid-base theory has several advantages over Ar-
rhenius theory. Consider the following reactions of acetic
acid (CH3 COOH), the organic acid that gives vinegar its
characteristic taste:

Svante Arrhenius CH
3COOH + H
The Swedish chemist Svante Arrhenius attributed the 2O CH
properties of acidity to hydrogen ions (H+ ) or protons 3COO
in 1884. An Arrhenius acid is a substance that, when +H
added to water, increases the concentration of H+ ions in 3O+
the water.[4][5] Note that chemists often write H+ (aq) and
refer to the hydrogen ion when describing acid-base re- CH
actions but the free hydrogen nucleus, a proton, does not 3COOH + NH
exist alone in water, it exists as the hydronium ion, H3 O+ . 3 CH
Thus, an Arrhenius acid can also be described as a sub- 3COO
stance that increases the concentration of hydronium ions + NH+
when added to water. Examples include molecular sub- 4
stances such as HCl and acetic acid.
An Arrhenius base, on the other hand, is a substance Both theories easily describe the rst reaction:
which increases the concentration of hydroxide (OH ) CH3 COOH acts as an Arrhenius acid because it
ions when dissolved in water. This decreases the con- acts as a source of H3 O+ when dissolved in water,
centration of hydronium because the ions react to form and it acts as a Brnsted acid by donating a proton to
H2 O molecules: water. In the second example CH3 COOH undergoes the
same transformation, in this case donating a proton to
H3 O+ + OH H2 O + H2 O ammonia (NH3 ), but does not relate to the Arrhenius
Due to this equilibrium, any increase in the concentration denition of an acid because the reaction does not
of hydronium is accompanied by a decrease in the con- produce hydronium. Nevertheless, CH3 COOH is both
centration of hydroxide. Thus, an Arrhenius acid could an Arrhenius and a Brnsted-Lowry acid.
also be said to be one that decreases hydroxide concen- Brnsted-Lowry theory can be used to describe reac-
tration, while an Arrhenius base increases it. tions of molecular compounds in nonaqueous solution
In an acidic solution, the concentration of hydronium ions or the gas phase. Hydrogen chloride (HCl) and ammo-
is greater than 107 moles per liter. Since pH is dened as nia combine under several dierent conditions to form

ammonium chloride, NH4 Cl. In aqueous solution HCl
behaves as hydrochloric acid and exists as hydronium and
chloride ions. The following reactions illustrate the limi-
tations of Arrheniuss denition:
1. H3 O+ + Cl + NH3 Cl + NH4 + + tron pair is the Lewis acid; for example, the oxygen atom
H2 O
2. HCl + NH NH4 Cl become localized on oxygen. Depending on the context,
3. HCl + NH NH4 Cl
As with the acetic acid reactions, both denitions work
for the rst example, where water is the solvent and hy-
dronium ion is formed by the HCl solute. The next two
reactions do not involve the formation of ions but are still
proton-transfer reactions. In the second reaction hydro-
gen chloride and ammonia (dissolved in benzene) react to
form solid ammonium chloride in a benzene solvent and
in the third gaseous HCl and NH3 combine to form the
solid.
1.3 Lewis acids
A third, only marginally related concept was proposed
in 1923 by Gilbert N. Lewis, which includes reactions
with acid-base characteristics that do not involve a pro-
ton transfer. A Lewis acid is a species that accepts a pair
of electrons from another species; in other words, it is
an electron pair acceptor.[5] Brnsted acid-base reactions
are proton transfer reactions while Lewis acid-base reac-
tions are electron pair transfers. Many Lewis acids are
not Brnsted-Lowry acids. Contrast how the following
reactions are described in terms of acid-base chemistry:
In the rst reaction a uoride ion, F , gives up an
electron pair to boron triuoride to form the product
tetrauoroborate. Fluoride loses a pair of valence elec-
trons because the electrons shared in the BF bond are
located in the region of space between the two atomic
nuclei and are therefore more distant from the uoride nu-
cleus than they are in the lone uoride ion. BF3 is a Lewis
acid because it accepts the electron pair from uoride.
This reaction cannot be described in terms of Brnsted
theory because there is no proton transfer. The second
3
reaction can be described using either theory. A proton
is transferred from an unspecied Brnsted acid to am-
monia, a Brnsted base; alternatively, ammonia acts as a
Lewis base and transfers a lone pair of electrons to form a
bond with a hydrogen ion. The species that gains the elec-
in H3 O+ gains a pair of electrons when one of the H
O bonds is broken and the electrons shared in the bond
a Lewis acid may also be described as an oxidizer or an
electrophile. Organic Brnsted acids, such as acetic, cit-
ric, or oxalic acid, are not Lewis acids.[4] They dissociate
in water to produce a Lewis acid, H+ , but at the same
time also yield an equal amount of a Lewis base (acetate,
citrate, or oxalate, respectively, for the acids mentioned).
Few, if any, of the acids discussed in the following are
Lewis acids.
2 Dissociation and equilibrium
Reactions of acids are often generalized in the form HA
H+ + A , where HA represents the acid and A is the
conjugate base. This reaction is referred to as protolysis.
The protonated form (HA) of an acid is also sometimes
referred to as the free acid.[6]
Acid-base conjugate pairs dier by one proton, and can
be interconverted by the addition or removal of a pro-
ton (protonation and deprotonation, respectively). Note
that the acid can be the charged species and the conjugate
base can be neutral in which case the generalized reaction
scheme could be written as HA+ H+ + A. In solution
there exists an equilibrium between the acid and its con-
jugate base. The equilibrium constant K is an expression
of the equilibrium concentrations of the molecules or the
ions in solution. Brackets indicate concentration, such
that [H2 O] means the concentration of H2 O. The acid dis-
sociation constant K is generally used in the context of
acid-base reactions. The numerical value of K is equal to
the product of the concentrations of the products divided
by the concentration of the reactants, where the reactant
is the acid (HA) and the products are the conjugate base
and H+ .
The stronger of two acids will have a higher K than the
weaker acid; the ratio of hydrogen ions to acid will be
higher for the stronger acid as the stronger acid has a
greater tendency to lose its proton. Because the range of
possible values for K spans many orders of magnitude, a
more manageable constant, pK is more frequently used,
where pK = log10 K. Stronger acids have a smaller pK
than weaker acids. Experimentally determined pK at 25
C in aqueous solution are often quoted in textbooks and
reference material.
4 5 CHEMICAL CHARACTERISTICS

3 Nomenclature compound in water is determined by the dilution of the

compound and the compounds K.
In the classical naming system, acids are named according
to their anions. That ionic sux is dropped and replaced
with a new sux (and sometimes prex), according to the 5 Chemical characteristics
table below. For example, HCl has chloride as its anion,
so the -ide sux makes it take the form hydrochloric acid. 5.1 Monoprotic acids
In the IUPAC naming system, aqueous is simply added
to the name of the ionic compound. Thus, for hydrogen Monoprotic acids are those acids that are able to do-
chloride, the IUPAC name would be aqueous hydrogen nate one proton per molecule during the process of
chloride. The prex hydro-" is added only if the acid is dissociation (sometimes called ionization) as shown be-
made up of just hydrogen and one other element. low (symbolized by HA):
Classical naming system:
HA + H2 O H3 O+ + A K

Common examples of monoprotic acids in mineral acids

4 Acid strength include hydrochloric acid (HCl) and nitric acid (HNO3 ).
On the other hand, for organic acids the term mainly in-
Main article: Acid strength dicates the presence of one carboxylic acid group and
sometimes these acids are known as monocarboxylic
acid. Examples in organic acids include formic acid
The strength of an acid refers to its ability or tendency to
(HCOOH), acetic acid (CH3 COOH) and benzoic acid
lose a proton. A strong acid is one that completely dis-
(C6 H5 COOH).
sociates in water; in other words, one mole of a strong
+
acid HA dissolves in water yielding one mole of H and See also: Acid dissociation constant Monoprotic acids
one mole of the conjugate base, A , and none of the
protonated acid HA. In contrast, a weak acid only par-
tially dissociates and at equilibrium both the acid and
the conjugate base are in solution. Examples of strong 5.2 Polyprotic acids
acids are hydrochloric acid (HCl), hydroiodic acid (HI),
hydrobromic acid (HBr), perchloric acid (HClO4 ), nitric Polyprotic acids, also known as polybasic acids, are able
acid (HNO3 ) and sulfuric acid (H2 SO4 ). In water each of to donate more than one proton per acid molecule, in con-
these essentially ionizes 100%. The stronger an acid is, trast to monoprotic acids that only donate one proton per
the more easily it loses a proton, H+ . Two key factors that molecule. Specic types of polyprotic acids have more
contribute to the ease of deprotonation are the polarity of specic names, such as diprotic acid (two potential pro-
the HA bond and the size of atom A, which determines tons to donate) and triprotic acid (three potential protons
the strength of the HA bond. Acid strengths are also to donate).
often discussed in terms of the stability of the conjugate A diprotic acid (here symbolized by H2 A) can undergo
base. one or two dissociations depending on the pH. Each dis-
Stronger acids have a larger K and a more negative pK sociation has its own dissociation constant, K and K.
than weaker acids.
H2 A + H2 O H3 O+ + HA K
Sulfonic acids, which are organic oxyacids, are a class
HA + H2 O H3 O+ + A2 K
of strong acids. A common example is toluenesulfonic
acid (tosylic acid). Unlike sulfuric acid itself, sulfonic The rst dissociation constant is typically greater than
acids can be solids. In fact, polystyrene functionalized the second; i.e., K > K. For example, sulfuric acid
into polystyrene sulfonate is a solid strongly acidic plastic (H2 SO4 ) can donate one proton to form the bisulfate an-
that is lterable. ion (HSO4 ), for which K is very large; then it can do-
Superacids are acids stronger than 100% sulfuric nate a second proton to form the sulfate anion (SO4 2 ),
acid. Examples of superacids are uoroantimonic wherein the K is intermediate strength. The large K
acid, magic acid and perchloric acid. Superacids can for the rst dissociation makes sulfuric a strong acid.
permanently protonate water to give ionic, crystalline In a similar manner, the weak unstable carbonic acid
hydronium salts. They can also quantitatively stabilize (H2 CO3 ) can lose one proton to form bicarbonate an-
carbocations. ion (HCO3 ) and lose a second to form carbonate anion
While K measures the strength of an acid compound, the (CO3 2 ). Both K values are small, but K > K .
strength of an aqueous acid solution is measured by pH, A triprotic acid (H3 A) can undergo one, two, or three
which is an indication of the concentration of hydronium dissociations and has three dissociation constants, where
in the solution. The pH of a simple solution of an acid K > K > K.
5.4 Weak acidweak base equilibrium 5

H3 A + H2 O H3 O+ + H2 A K
H2 A + H2 O H3 O+ + HA2 K
HA2 + H2 O H3 O+ + A3 K

An inorganic example of a triprotic acid is orthophospho-

ric acid (H3 PO4 ), usually just called phosphoric acid. All
three protons can be successively lost to yield H2 PO4 ,
then HPO4 2 , and nally PO4 3 , the orthophosphate ion,
usually just called phosphate. Even though the posi-
tions of the three protons on the original phosphoric acid
molecule are equivalent, the successive K values dier
since it is energetically less favorable to lose a proton
if the conjugate base is more negatively charged. An
organic example of a triprotic acid is citric acid, which
can successively lose three protons to nally form the
citrate ion.
Although the subsequent loss of each hydrogen ion is less
favorable, all of the conjugate bases are present in so- Hydrochloric acid (in beaker) reacting with ammonia fumes to
lution. The fractional concentration, (alpha), for each produce ammonium chloride (white smoke).
species can be calculated. For example, a generic diprotic
acid will generate 3 species in solution: H2 A, HA , and Conversely, neutralizing a weak acid with a strong base
A2 . The fractional concentrations can be calculated as gives a weakly basic salt, e.g. sodium uoride from
below when given either the pH (which can be converted hydrogen uoride and sodium hydroxide.
to the [H+ ]) or the concentrations of the acid with all its
conjugate bases:
A plot of these fractional concentrations against pH, for
5.4 Weak acidweak base equilibrium
given K 1 and K 2 , is known as a Bjerrum plot. A pattern
Main article: HendersonHasselbalch equation
is observed in the above equations and can be expanded
to the general n -protic acid that has been deprotonated i
-times: In order for a protonated acid to lose a proton, the pH of
the system must rise above the pK of the acid. The de-
where K 0 = 1 and the other K-terms are the dissociation
creased concentration of H+ in that basic solution shifts
constants for the acid.
the equilibrium towards the conjugate base form (the de-
See also: Acid dissociation constant Polyprotic acids protonated 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.

5.3 Neutralization Solutions of weak acids and salts of their conjugate bases
form buer solutions.
Neutralization is the reaction between an acid and a
base, producing a salt and neutralized base; for example,
hydrochloric acid and sodium hydroxide form sodium 6 Applications of acids
chloride and water:
There are numerous uses for acids. Acids are often used
HCl + NaOH H2 O + NaCl to remove rust and other corrosion from metals in a pro-
cess known as pickling. They may be used as an elec-
Neutralization is the basis of titration, where a pH indica- trolyte in a wet cell battery, such as sulfuric acid in a car
tor shows equivalence point when the equivalent number battery.
of moles of a base have been added to an acid. It is of- Strong acids, sulfuric acid in particular, are widely used
ten wrongly assumed that neutralization should result in a in mineral processing. For example, phosphate minerals
solution with pH 7.0, which is only the case with similar react with sulfuric acid to produce phosphoric acid for the
acid and base strengths during a reaction. production of phosphate fertilizers, and zinc is produced
Neutralization with a base weaker than the acid results by dissolving zinc oxide into sulfuric acid, purifying the
in a weakly acidic salt. An example is the weakly acidic solution and electrowinning.
ammonium chloride, which is produced from the strong In the chemical industry, acids react in neutralization re-
acid hydrogen chloride and the weak base ammonia. actions to produce salts. For example, nitric acid reacts
6 7 BIOLOGICAL OCCURRENCE

with ammonia to produce ammonium nitrate, a fertilizer.

Additionally, carboxylic acids can be esteried with alco-
hols, to produce esters.
Acids are used as additives to drinks and foods, as they
alter their taste and serve as preservatives. Phosphoric
acid, for example, is a component of cola drinks. Acetic
acid is used in day-to-day life as vinegar. Carbonic acid
is an important part of some cola drinks and soda. Citric
acid is used as a preservative in sauces and pickles.
Tartaric acid is an important component of some com-
monly used foods like unripened mangoes and tamarind.
Natural fruits and vegetables also contain acids. Citric
acid is present in oranges, lemon and other citrus fruits.
Oxalic acid is present in tomatoes, spinach, and espe-
cially in carambola and rhubarb; rhubarb leaves and un-
Basic structure of an amino acid.
ripe carambolas are toxic because of high concentrations
of oxalic acid.
Ascorbic acid (Vitamin C) is an essential vitamin for the units. Cell membranes contain fatty acid esters such as
human body and is present in such foods as amla (Indian phospholipids.
gooseberry), lemon, citrus fruits, and guava.
An -amino acid has a central carbon (the or alpha
Certain acids are used as drugs. Acetylsalicylic acid (As- carbon) which is covalently bonded to a carboxyl group
pirin) is used as a pain killer and for bringing down fevers. (thus they are carboxylic acids), an amino group, a hy-
Acids play important roles in the human body. The hy- drogen atom and a variable group. The variable group,
drochloric acid present in the stomach aids in digestion also called the R group or side chain, determines the iden-
by breaking down large and complex food molecules. tity and many of the properties of a specic amino acid.
Amino acids are required for synthesis of proteins re- In glycine, the simplest amino acid, the R group is a hy-
quired for growth and repair of body tissues. Fatty acids drogen atom, but in all other amino acids it is contains
are also required for growth and repair of body tissues. one or more carbon atoms bonded to hydrogens, and may
Nucleic acids are important for the manufacturing of contain other elements such as sulfur, oxygen or nitro-
DNA and RNA and transmitting of traits to ospring gen. With the exception of glycine, naturally occurring
through genes. Carbonic acid is important for mainte- amino acids are chiral and almost invariably occur in the
nance of pH equilibrium in the body. L-conguration. Peptidoglycan, found in some bacterial
cell walls contains some D-amino acids. At physiological
pH, typically around 7, free amino acids exist in a charged
form, where the acidic carboxyl group (-COOH) loses a
6.1 Acid catalysis
proton (-COO ) and the basic amine group (-NH2 ) gains
a proton (-NH3 + ). The entire molecule has a net neutral
Main article: Acid catalysis
charge and is a zwitterion, with the exception of amino
acids with basic or acidic side chains. Aspartic acid, for
Acids are used as catalysts in industrial and organic chem- example, possesses one protonated amine and two depro-
istry; for example, sulfuric acid is used in very large quan- tonated carboxyl groups, for a net charge of 1 at physi-
tities in the alkylation process to produce gasoline. Strong ological pH.
acids, such as sulfuric, phosphoric and hydrochloric acids
Fatty acids and fatty acid derivatives are another group
also eect dehydration and condensation reactions. In
of carboxylic acids that play a signicant role in biology.
biochemistry, many enzymes employ acid catalysis.[7]
These contain long hydrocarbon chains and a carboxylic
acid group on one end. The cell membrane of nearly all
organisms is primarily made up of a phospholipid bilayer,
7 Biological occurrence a micelle of hydrophobic fatty acid esters with polar, hy-
drophilic phosphate head groups. Membranes contain
Many biologically important molecules are acids. additional components, some of which can participate in
Nucleic acids, which contain acidic phosphate groups, acid-base reactions.
include DNA and RNA. Nucleic acids contain the In humans and many other animals, hydrochloric acid is
genetic code that determines many of an organisms a part of the gastric acid secreted within the stomach to
characteristics, and is passed from parents to ospring. help hydrolyze proteins and polysaccharides, as well as
DNA contains the chemical blueprint for the synthesis converting the inactive pro-enzyme, pepsinogen into the
of proteins which are made up of amino acid sub- enzyme, pepsin. Some organisms produce acids for de-
 7

fense; for example, ants produce formic acid. 8 Common acids

Acid-base equilibrium plays a critical role in regulat-
ing mammalian breathing. Oxygen gas (O2 ) drives 8.1 Mineral acids (inorganic acids)
cellular respiration, the process by which animals release
the chemical potential energy stored in food, producing
carbon dioxide (CO2 ) as a byproduct. Oxygen and car-
bon dioxide are exchanged in the lungs, and the body
responds to changing energy demands by adjusting the
rate of ventilation. For example, during periods of exer-
tion the body rapidly breaks down stored carbohydrates
and fat, releasing CO2 into the blood stream. In aqueous
solutions such as blood CO2 exists in equilibrium with
carbonic acid and bicarbonate ion.
Hydrogen halides and their solutions: hydrouoric
acid (HF), hydrochloric acid (HCl), hydrobromic
acid (HBr), hydroiodic acid (HI)
Halogen oxoacids: hypochlorous acid (HClO),
chlorous acid (HClO2 ), chloric acid (HClO3 ),
perchloric acid (HClO4 ), and corresponding com-
pounds for bromine and iodine
Sulfuric acid (H2 SO4 )

Fluorosulfuric acid (HSO3 F)

CO2 + H2 O H2 CO3 H+ + HCO3
Nitric acid (HNO3 )
It is the decrease in pH that signals the brain to breathe Phosphoric acid (H3 PO4 )
faster and deeper, expelling the excess CO2 and resup-
plying the cells with O2 . Fluoroantimonic acid (HSbF6 )

Fluoroboric acid (HBF4 )

O OH Hexauorophosphoric acid (HPF6 )

Chromic acid (H2 CrO4 )

Boric acid (H3 BO3 )

O 8.2 Sulfonic acids

A sulfonic acid has the general formula RS(=O)2 OH,
where R is an organic radical.

O Methanesulfonic acid (or mesylic acid, CH3 SO3 H)

Ethanesulfonic acid (or esylic acid, CH3 CH2 SO3 H)

Aspirin (acetylsalicylic acid) is a carboxylic acid. Benzenesulfonic acid (or besylic acid, C6 H5 SO3 H)

Cell membranes are generally impermeable to charged p-Toluenesulfonic acid (or tosylic acid,
or large, polar molecules because of the lipophilic fatty CH3 C6 H4 SO3 H)
acyl chains comprising their interior. Many biologically
Triuoromethanesulfonic acid (or triic acid,
important molecules, including a number of pharmaceu-
CF3 SO3 H)
tical agents, are organic weak acids which can cross the
membrane in their protonated, uncharged form but not Polystyrene sulfonic acid (sulfonated polystyrene,
in their charged form (i.e. as the conjugate base). For [CH2 CH(C6 H4 )SO3 H] )
this reason the activity of many drugs can be enhanced
or inhibited by the use of antacids or acidic foods. The
charged form, however, is often more soluble in blood 8.3 Carboxylic acids
and cytosol, both aqueous environments. When the ex-
tracellular environment is more acidic than the neutral A carboxylic acid has the general formula R-C(O)OH,
pH within the cell, certain acids will exist in their neu- where R is an organic radical. The carboxyl group -
tral form and will be membrane soluble, allowing them to C(O)OH contains a carbonyl group, C=O, and a hydroxyl
cross the phospholipid bilayer. Acids that lose a proton group, O-H.
at the intracellular pH will exist in their soluble, charged
form and are thus able to diuse through the cytosol to Acetic acid (CH3 COOH)
their target. Ibuprofen, aspirin and penicillin are exam-
ples of drugs that are weak acids. Citric acid (C6 H8 O7 )
8 10 EXTERNAL LINKS

Formic acid (HCOOH) [6] Stahl PH, Nakamo M (2008). Pharmaceutical Aspects
of the Salt Form. In Stahl PH, Warmth CG. Hand-
Gluconic acid HOCH2 -(CHOH)4 -COOH book of Pharmaceutical Salts: Properties, Selection, and
Use. Weinheim: Wiley-VCH. pp. 9294. ISBN 978-3-
Lactic acid (CH3 -CHOH-COOH) 906390-58-1.

Oxalic acid (HOOC-COOH) [7] Voet, Judith G.; Voet, Donald (2004). Biochemistry. New
York: J. Wiley & Sons. pp. 496500. ISBN 978-0-471-
Tartaric acid (HOOC-CHOH-CHOH-COOH) 19350-0.

Listing of strengths of common acids and bases

8.4 Halogenated carboxylic acids
IUPAC Gold Book - acid
Halogenation at alpha position increases acid strength, so
Zumdahl, Chemistry, 4th Edition.
that the following acids are all stronger than acetic acid.
Ebbing, D.D., & Gammon, S. D. (2005). General
Fluoroacetic acid chemistry (8th ed.). Boston, MA: Houghton Miin.
ISBN 0-618-51177-6
Triuoroacetic acid
Pavia, D.L., Lampman, G.M., & Kriz, G.S. (2004).
Chloroacetic acid Organic chemistry volume 1: Organic chemistry 351.
Mason, OH: Cenage Learning. ISBN 0-7593-4727-
Dichloroacetic acid 1
Trichloroacetic acid
10 External links
8.5 Vinylogous carboxylic acids
Science Aid: Acids and Bases Information for High
Normal carboxylic acids are the direct union of a car- School students
bonyl group and a hydroxyl group. In vinylogous car-
Curtipot: Acid-Base equilibria diagrams, pH calcu-
boxylic acids, a carbon-carbon double bond separates the
lation and titration curves simulation and analysis
carbonyl and hydroxyl groups.
freeware

Ascorbic acid A summary of the Properties of Acids for the begin-

ning chemistry student
The UN ECE Convention on Long-Range Trans-
8.6 Nucleic acids
boundary Air Pollution
Deoxyribonucleic acid (DNA) Chem 106 Acidity Concepts
Ribonucleic acid (RNA)

9 References
[1] IUPAC Gold Book - acid

[2] Petrucci R.H., Harwood, R.S. and Herring, F.G. General

Chemistry (8th ed., Prentice-Hall 2002) p.146 ISBN 0-13-
014329-4

[3] Merriam-Websters Online Dictionary: acid

[4] Oxtoby, D. W; Gillis, H.P., Butler, L. J. (2015).Principles

of Modern Chemistry, Brooks Cole. p. 617. ISBN 978-
1305079113

[5] Ebbing, D.D., & Gammon, S. D. (2005). General chem-

istry (8th ed.). Boston, MA: Houghton Miin. ISBN 0-
618-51177-6
 9

11 Text and image sources, contributors, and licenses

11.1 Text
Acid Source: https://en.wikipedia.org/wiki/Acid?oldid=746214370 Contributors: Damian Yerrick, Derek Ross, Sodium, Bryan Derk-
sen, MarXidad, Tarquin, Andre Engels, Anthere, Rmrf1024, Heron, Hfastedge, Bdesham, PhilipMW, Michael Hardy, Shellreef, Ixfd64,
Fruge~enwiki, Markonen, Card~enwiki, Ahoerstemeier, Mac, Darkwind, , Andres, Tristanb, Uyanga, Zarius, Ideyal, Emper-
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Borg, Uopchem253, Uopchem25 7, W192, Meghas2, SaadTeenager, Yazan kokash, ChrisGualtieri, Abdulwahabmalik, Webclient101,
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ditya and Anonymous: 1024
10 11 TEXT AND IMAGE SOURCES, CONTRIBUTORS, AND LICENSES

11.2 Images
File:Acetic-acid-dissociation-3D-balls.png Source: https://upload.wikimedia.org/wikipedia/commons/9/96/
Acetic-acid-dissociation-3D-balls.png License: Public domain Contributors: Own work Original artist: Ben Mills
File:Aminoacid.png Source: https://upload.wikimedia.org/wikipedia/commons/3/34/Aminoacid.png License: Public domain Contribu-
tors: made in MarvinSketch Original artist: Myceteae
File:Arrhenius2.jpg Source: https://upload.wikimedia.org/wikipedia/commons/6/6c/Arrhenius2.jpg License: Public domain Contribu-
tors: ? Original artist: ?
File:Aspirin-skeletal.svg Source: https://upload.wikimedia.org/wikipedia/commons/6/67/Aspirin-skeletal.svg License: Public domain
Contributors: SVG conversion of Image:Aspirin-skeletal.png Original artist: Originally User:Benjah-bmm27
File:Hydrochloric_acid_ammonia.jpg Source: https://upload.wikimedia.org/wikipedia/commons/a/a0/Hydrochloric_acid_ammonia.
jpg License: Public domain Contributors: ? Original artist: ?
File:LewisAcid.png Source: https://upload.wikimedia.org/wikipedia/commons/4/4d/LewisAcid.png License: Public domain Contribu-
tors: made in jchempaint, modied in Pixen Original artist: Myceteae
File:Text_document_with_red_question_mark.svg Source: https://upload.wikimedia.org/wikipedia/commons/a/a4/Text_document_
with_red_question_mark.svg License: Public domain Contributors: Created by bdesham with Inkscape; based upon Text-x-generic.svg
from the Tango project. Original artist: Benjamin D. Esham (bdesham)
File:Zn_reaction_with_HCl.JPG Source: https://upload.wikimedia.org/wikipedia/commons/d/d4/Zn_reaction_with_HCl.JPG License:
Public domain Contributors: Own work Original artist: Chemicalinterest

11.3 Content license

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