A chemical nomenclature is a set of rules to generate systematic names for
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one ele ...
s. The nomenclature used most frequently worldwide is the one created and developed by the
International Union of Pure and Applied Chemistry
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
inorganic compound
In chemistry, an inorganic compound is typically a chemical compound that lacks carbon–hydrogen bonds, that is, a compound that is not an organic compound. The study of inorganic compounds is a subfield of chemistry known as '' inorganic chemi ...
s are contained in two publications, known as the '' Blue Book''. . and the '' Red Book'',. respectively. A third publication, known as the '' Green Book'',. recommends the use of
symbol
A symbol is a mark, sign, or word that indicates, signifies, or is understood as representing an idea, object, or relationship. Symbols allow people to go beyond what is known or seen by creating linkages between otherwise very different conc ...
s for
physical quantities
A physical quantity is a physical property of a material or system that can be quantified by measurement. A physical quantity can be expressed as a ''value'', which is the algebraic multiplication of a ' Numerical value ' and a ' Unit '. For examp ...
(in association with the IUPAP), while a fourth, the '' Gold Book'',''Compendium of Chemical Terminology, IMPACT Recommendations (2nd Ed.)'', Oxford:Blackwell Scientific Publications. (1997) defines many technical terms used in chemistry. Similar compendia exist for
biochemistry
Biochemistry or biological chemistry is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology ...
''Biochemical Nomenclature and Related Documents'', London: Portland Press, 1992. (the ''White Book'', in association with the IUBMB),
analytical chemistry
Analytical chemistry studies and uses instruments and methods to separate, identify, and quantify matter. In practice, separation, identification or quantification may constitute the entire analysis or be combined with another method. Separati ...
(the '' Orange Book''), macromolecular chemistry''Compendium of Macromolecular Nomenclature'', Oxford: Blackwell Scientific Publications, 1991. (the ''Purple Book''), and
clinical chemistry
Clinical chemistry (also known as chemical pathology, clinical biochemistry or medical biochemistry) is the area of chemistry that is generally concerned with analysis of bodily fluids for diagnostic and therapeutic purposes. It is an appli ...
. (the ''Silver Book''). These "color books" are supplemented by specific recommendations published periodically in the journal ''
Pure and Applied Chemistry
''Pure and Applied Chemistry'' is the official journal for the International Union of Pure and Applied Chemistry (IUPAC). It is published monthly by Walter de Gruyter
Walter de Gruyter GmbH, known as De Gruyter (), is a German scholarly pub ...
''.
Aims of chemical nomenclature
The main goal of chemical nomenclature is to disambiguate the spoken or written names of chemical compounds: each name should refer to one compound. Secondarily: each compound should have only one name, although in some cases some alternative names are accepted.
Preferably, the name should also reflect the structure or chemistry of a compound. This is achieved by the International Chemical Identifier (InChI) nomenclature. However, the
American Chemical Society
The American Chemical Society (ACS) is a scientific society based in the United States that supports scientific inquiry in the field of chemistry. Founded in 1876 at New York University, the ACS currently has more than 155,000 members at all ...
's CAS numbers nomenclature reflects nothing of the compound's structure.
The nomenclature used depends on the needs of the user, so no single correct nomenclature exists. Rather, different nomenclatures suit different circumstances.
A
common name
In biology, a common name of a taxon or organism (also known as a vernacular name, English name, colloquial name, country name, popular name, or farmer's name) is a name that is based on the normal language of everyday life; and is often contra ...
will successfully identify a chemical compound, given context. Without context, the name should indicate at least the chemical composition. To be more specific, the name may need to reflect the three-dimensional arrangement of the atoms.This requires adding more rules to the standard IUPAC system (the CAS system is the most commonly used in this context), at the expense of having longer and less familiar names.
The IUPAC system is often criticized for the failing to distinguish relevant compounds (for example, in differing reactivity of sulfur allotropes, which IUPAC does not distinguish). While IUPAC has a human-readable advantage over CAS numbering, IUPAC names for some larger, relevant molecules (such as
rapamycin
Sirolimus, also known as rapamycin and sold under the brand name Rapamune among others, is a macrolide compound that is used to coat coronary stents, prevent organ transplant rejection, treat a rare lung disease called lymphangioleiomyomatosi ...
) are barely human-readable, so common names are used instead.
Differing aims of chemical nomenclature and lexicography
It is generally understood that the aims of
lexicography
Lexicography is the study of lexicons, and is divided into two separate academic disciplines. It is the art of compiling dictionaries.
* Practical lexicography is the art or craft of compiling, writing and editing dictionaries.
* Theoret ...
versus chemical nomenclature vary and are to an extent at odds. Dictionaries of words, whether in traditional print or on the web, collect and report the meanings of words as their uses appear and change over time. For web dictionaries with limited or no formal editorial process, definitions —in this case, definitions of chemical names and terms— can change rapidly without concern for the formal or historical meanings. Chemical nomenclature on the other hand (with
IUPAC
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
nomenclature as the best example) is necessarily more restrictive: It aims to standardize communication and practice so that, when a chemical term is used it has a fixed meaning relating to chemical structure, thereby giving insights into chemical properties and derived molecular functions. These differing aims can have profound effects on valid understanding in chemistry, especially with regard to chemical classes that have achieved mass attention. Examples of the impact of these can be seen in considering the examples of:
*
resveratrol
Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources ...
, a single compound clearly defined by this common name, but that can be confused, popularly, with its ''cis''-isomer,
*
omega-3 fatty acids
Omega−3 fatty acids, also called Omega-3 oils, ω−3 fatty acids or ''n''−3 fatty acids, are polyunsaturated fatty acids (PUFAs) characterized by the presence of a double bond, three atoms away from the terminal methyl group in their che ...
, a reasonably well-defined chemical structure class that is nevertheless broad as a result of its formal definition, and
*
polyphenol
Polyphenols () are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some o ...
s, a fairly broad structural class with a formal definition, but where mistranslations and general misuse of the term relative to the formal definition has led to serious usage errors, and so ambiguity in the relationship between structure and activity ( SAR).
The rapid pace at which meanings can change on the web, in particular for chemical compounds with perceived health benefits, rightly or wrongly ascribed, complicate the monosemy of nomenclature (and so access to SAR understanding). Specific examples appear on the
polyphenol
Polyphenols () are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some o ...
s article, where varying web and common-use definitions conflict with any accepted chemical nomenclature connecting polyphenol structure and bioactivity).
History
The nomenclature of
alchemy
Alchemy (from Arabic: ''al-kīmiyā''; from Ancient Greek: χυμεία, ''khumeía'') is an ancient branch of natural philosophy, a philosophical and protoscientific tradition that was historically practiced in China, India, the Muslim world ...
is rich in description, but does not effectively meet the aims outlined above. Opinions differ about whether this was deliberate on the part of the early practitioners of alchemy or whether it was a consequence of the particular (and often esoteric) theoretical framework in which they worked.
While both explanations are probably valid to some extent, it is remarkable that the first "modern" system of chemical nomenclature appeared at the same time as the distinction (by
Lavoisier
Antoine-Laurent de Lavoisier ( , ; ; 26 August 17438 May 1794), CNRS ( elements
Element or elements may refer to:
Science
* Chemical element, a pure substance of one type of atom
* Heating element, a device that generates heat by electrical resistance
* Orbital elements, parameters required to identify a specific orbit of ...
and compounds, in the late eighteenth century.
The
French
French (french: français(e), link=no) may refer to:
* Something of, from, or related to France
** French language, which originated in France, and its various dialects and accents
** French people, a nation and ethnic group identified with Franc ...
chemist Louis-Bernard Guyton de Morveau published his recommendations in 1782, hoping that his "constant method of denomination" would "help the intelligence and relieve the memory". The system was refined in collaboration with
Berthollet
Claude Louis Berthollet (, 9 December 1748 – 6 November 1822) was a Savoyard-French chemist who became vice president of the French Senate in 1804. He is known for his scientific contributions to theory of chemical equilibria via the mec ...
Lavoisier
Antoine-Laurent de Lavoisier ( , ; ; 26 August 17438 May 1794), CNRS ( . and promoted by the latter in a textbook that would survive long after his death at the
guillotine
A guillotine is an apparatus designed for efficiently carrying out executions by beheading. The device consists of a tall, upright frame with a weighted and angled blade suspended at the top. The condemned person is secured with stocks at t ...
in 1794.. The project was also espoused by Jöns Jakob Berzelius,.. who adapted the ideas for the German-speaking world.
The recommendations of Guyton covered only what would be today known as inorganic compounds. With the massive expansion of organic chemistry in the mid-nineteenth century and the greater understanding of the structure of organic compounds, the need for a less ''ad hoc'' system of nomenclature was felt just as the theoretical tools became available to make this possible. An international conference was convened in
Geneva
Geneva ( ; french: Genève ) frp, Genèva ; german: link=no, Genf ; it, Ginevra ; rm, Genevra is the second-most populous city in Switzerland (after Zürich) and the most populous city of Romandy, the French-speaking part of Switzerland. Situ ...
in 1892 by the national chemical societies, from which the first widely accepted proposals for standardization arose..
A commission was set up in 1913 by the Council of the International Association of Chemical Societies, but its work was interrupted by
World War I
World War I (28 July 1914 11 November 1918), often abbreviated as WWI, was List of wars and anthropogenic disasters by death toll, one of the deadliest global conflicts in history. Belligerents included much of Europe, the Russian Empire, ...
. After the war, the task passed to the newly formed
International Union of Pure and Applied Chemistry
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
, which first appointed commissions for organic, inorganic, and biochemical nomenclature in 1921 and continues to do so to this day.
Types of nomenclature
Organic chemistry
* Substitutive name
* Functional class name, also known as a radicofunctional name
* Conjunctive name
* Additive name
* Subtractive name
* Multiplicative name
* Fusion name
* Hantzsch–Widman name
* Replacement name
cation
An ion () is an atom or molecule with a net electrical charge.
The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conve ...
(a
metal
A metal (from Greek μέταλλον ''métallon'', "mine, quarry, metal") is a material that, when freshly prepared, polished, or fractured, shows a lustrous appearance, and conducts electricity and heat relatively well. Metals are typi ...
in most cases) is named first, and the
anion
An ion () is an atom or molecule with a net electrical charge.
The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conve ...
(usually a
nonmetal
In chemistry, a nonmetal is a chemical element that generally lacks a predominance of metallic properties; they range from colorless gases (like hydrogen) to shiny solids (like carbon, as graphite). The electrons in nonmetals behave differen ...
) is named second. The cation retains its elemental name (e.g., ''iron'' or ''zinc''), but the suffix of the nonmetal changes to ''-ide''. For example, the compound is made of cations and anions; thus, it's called lithium bromide. The compound , which is composed of cations and anions, is referred to as barium oxide.
The
oxidation state
In chemistry, the oxidation state, or oxidation number, is the hypothetical charge of an atom if all of its bonds to different atoms were fully ionic. It describes the degree of oxidation (loss of electrons) of an atom in a chemical compound. ...
of each element is unambiguous. When these ions combine into a type-I binary compound, their equal-but-opposite charges are neutralized, so the compound's net charge is zero.
= Type-II ionic binary compounds
=
Type-II ionic binary compounds are those in which the cation does not have just one oxidation state. This is common among transition metals. To name these compounds, one must determine the charge of the cation and then write out the name as would be done with Type-I ionic compounds, except that a
Roman numeral
Roman numerals are a numeral system that originated in ancient Rome and remained the usual way of writing numbers throughout Europe well into the Late Middle Ages. Numbers are written with combinations of letters from the Latin alphabet, eac ...
(indicating the charge of the cation) is written in parentheses next to the cation name (this is sometimes referred to as
Stock nomenclature
Stock nomenclature for inorganic compounds is a widely used system of chemical nomenclature developed by the German chemist Alfred Stock and first published in 1919. In the "Stock system", the oxidation states of some or all of the elements in a ...
). For example, take the compound . The cation,
iron
Iron () is a chemical element with symbol Fe (from la, ferrum) and atomic number 26. It is a metal that belongs to the first transition series and group 8 of the periodic table. It is, by mass, the most common element on Earth, right in ...
, can occur as and . In order for the compound to have a net charge of zero, the cation must be so that the three anions can be balanced out (3+ and 3− balance to 0). Thus, this compound is called iron(III) chloride. Another example could be the compound . Because the anion has a subscript of 2 in the formula (giving a 4− charge), the compound must be balanced with a 4+ charge on the cation (
lead
Lead is a chemical element with the Symbol (chemistry), symbol Pb (from the Latin ) and atomic number 82. It is a heavy metals, heavy metal that is density, denser than most common materials. Lead is Mohs scale of mineral hardness#Intermediate ...
can form cations with a 4+ or a 2+ charge). Thus, the compound is made of one cation to every two anions, the compound is balanced, and its name is written as
lead(IV) sulfide
Lead(IV) sulfide is a chemical compound with the formula Pb S2. This material is generated by the reaction of the more common lead(II) sulfide, PbS, with sulfur at >600 °C and at high pressures. PbS2, like the related tin(IV) sulfide SnS2, cryst ...
.
An older system – relying on Latin names for the elements – is also sometimes used to name Type-II ionic binary compounds. In this system, the metal (instead of a Roman numeral next to it) has an "-ic" or "-ous" suffix added to it to indicate its oxidation state ("-ous" for lower, "-ic" for higher). For example, the compound contains the cation (which balances out with the anion). Since this oxidation state is lower than the other possibility (), this compound is sometimes called ferrous oxide. For the compound, , the tin ion is (balancing out the 4− charge on the two anions), and because this is a higher oxidation state than the alternative (), this compound is called
stannic oxide
Tin(IV) oxide, also known as stannic oxide, is the inorganic compound with the formula SnO2. The mineral form of SnO2 is called cassiterite, and this is the main ore of tin. With many other names, this oxide of tin is an important material in tin ...
.
Some ionic compounds contain polyatomic ions, which are charged entities containing two or more covalently bonded types of atoms. It is important to know the names of common polyatomic ions; these include:
*
ammonium
The ammonium cation is a positively-charged polyatomic ion with the chemical formula or . It is formed by the protonation of ammonia (). Ammonium is also a general name for positively charged or protonated substituted amines and quaternar ...
()
*
nitrite
The nitrite ion has the chemical formula . Nitrite (mostly sodium nitrite) is widely used throughout chemical and pharmaceutical industries. The nitrite anion is a pervasive intermediate in the nitrogen cycle in nature. The name nitrite also re ...
()
*
nitrate
Nitrate is a polyatomic ion with the chemical formula . Salts containing this ion are called nitrates. Nitrates are common components of fertilizers and explosives. Almost all inorganic nitrates are soluble in water. An example of an insoluble ...
sulfate
The sulfate or sulphate ion is a polyatomic ion, polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salt (chemistry), ...
hydroxide
Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water ...
()
*
cyanide
Cyanide is a naturally occurring, rapidly acting, toxic chemical that can exist in many different forms.
In chemistry, a cyanide () is a chemical compound that contains a functional group. This group, known as the cyano group, consists of ...
()
*
phosphate
In chemistry, a phosphate is an anion, salt, functional group or ester derived from a phosphoric acid. It most commonly means orthophosphate, a derivative of orthophosphoric acid .
The phosphate or orthophosphate ion is derived from phosph ...
carbonate
A carbonate is a salt of carbonic acid (H2CO3), characterized by the presence of the carbonate ion, a polyatomic ion with the formula . The word ''carbonate'' may also refer to a carbonate ester, an organic compound containing the carbonat ...
()
*
hydrogen carbonate
In inorganic chemistry, bicarbonate (IUPAC-recommended nomenclature: hydrogencarbonate) is an intermediate form in the deprotonation of carbonic acid. It is a polyatomic anion with the chemical formula .
Bicarbonate serves a crucial biochemica ...
chlorate
The chlorate anion has the formula ClO3-. In this case, the chlorine atom is in the +5 oxidation state. "Chlorate" can also refer to chemical compounds containing this anion; chlorates are the salts of chloric acid. "Chlorate", when followe ...
()
*
perchlorate
A perchlorate is a chemical compound containing the perchlorate ion, . The majority of perchlorates are commercially produced salts. They are mainly used as oxidizers for pyrotechnic devices and to control static electricity in food packaging. ...
()
*
acetate
An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic or radical base). "Acetate" also describes the conjugate base or ion (specifically, the negatively charged ion called ...
peroxide
In chemistry, peroxides are a group of compounds with the structure , where R = any element. The group in a peroxide is called the peroxide group or peroxo group. The nomenclature is somewhat variable.
The most common peroxide is hydrogen ...
hydrogen oxalate
Hydrogenoxalate or hydrogen oxalate is an anion with chemical formula or , derived from oxalic acid by the loss of a single proton; or, alternatively, from the oxalate anion by addition of a proton. The name is also used for any salt containing ...
()
The formula denotes that the cation is
sodium
Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable ...
, or , and that the anion is the sulfite ion (). Therefore, this compound is named sodium sulfite. If the given formula is , it can be seen that is the hydroxide ion. Since the charge on the calcium ion is 2+, it makes sense there must be two ions to balance the charge. Therefore, the name of the compound is
calcium hydroxide
Calcium hydroxide (traditionally called slaked lime) is an inorganic compound with the chemical formula Ca( OH)2. It is a colorless crystal or white powder and is produced when quicklime ( calcium oxide) is mixed or slaked with water. It has m ...
. If one is asked to write the formula for copper(I) chromate, the Roman numeral indicates that copper ion is and one can identify that the compound contains the chromate ion (). Two of the 1+ copper ions are needed to balance the charge of one 2− chromate ion, so the formula is .
= Type-III binary compounds
=
Type-III binary compounds are covalently bonded. Covalent bonding occurs between nonmetal elements. Covalently-bonded compounds are also known as ''
molecule
A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bio ...
s''. In the compound, the first element is named first and with its full elemental name. The second element is named as if it were an anion (root name of the element + ''-ide'' suffix). Then, prefixes are used to indicate the numbers of each atom present: these prefixes are ''mono-'' (one), ''di-'' (two), ''tri-'' (three), ''tetra-'' (four), ''penta-'' (five), ''hexa-'' (six), ''hepta-'' (seven), ''octa-'' (eight), ''nona-'' (nine), and ''deca-'' (ten). The prefix ''mono-'' is never used with the first element. Thus, is called nitrogen trichloride, is called
diphosphorus pentaoxide
Diphosphorus is an inorganic chemical with the chemical formula . Unlike nitrogen, its lighter pnictogen neighbor which forms a stable N2 molecule with a nitrogen to nitrogen triple bond, phosphorus prefers a tetrahedral form P4 because P-P pi-bo ...
(the ''a'' of the ''penta-'' prefix is not dropped before the vowel. As the IUPAC Red Book 2005 page 69 states, "The final vowels of multiplicative prefixes should not be elided (although "monoxide", rather than "monooxide", is an allowed exception because of general usage."), and is called
boron trifluoride
Boron trifluoride is the inorganic compound with the formula BF3. This pungent, colourless, and toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds.
Structure and bondin ...
.
Carbon dioxide
Carbon dioxide ( chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is t ...
is written ;
sulfur tetrafluoride
Sulfur tetrafluoride is the chemical compound with the formula S F4. It is a colorless corrosive gas that releases dangerous HF upon exposure to water or moisture. Despite these unwelcome characteristics, this compound is a useful reagent for ...
is written . A few compounds, however, have common names that prevail. , for example, is usually called ''
water
Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as ...
ammonia
Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogeno ...
'' rather than ''nitrogen trihydride''.
Substitutive nomenclature
This naming method generally follows established IUPAC organic nomenclature. Hydrides of the main group elements (groups 13–17) are given ''-ane'' base name, e.g.
borane
Trihydridoboron, also known as borane or borine, is an unstable and highly reactive molecule with the chemical formula . The preparation of borane carbonyl, BH3(CO), played an important role in exploring the chemistry of boranes, as it indicated ...
phosphine
Phosphine ( IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotti ...
'' is also in common use, it is not recommended by IUPAC). The compound would thus be named substitutively as trichlorophosphane (with chlorine "substituting"). However, not all such names (or stems) are derived from the element name. For example, is called " azane".
Additive nomenclature
This naming method has been developed principally for coordination compounds although it can be more widely applied. An example of its application is , pentaamminechloridocobalt(III) chloride.
Ligand
In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's ele ...
s, too, have a special naming convention. Whereas ''chloride'' becomes the prefix ''chloro-'' in substitutive naming, in a ligand it becomes ''chlorido-''.
IUPAC nomenclature of organic chemistry
In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the '' Nomenclature of ...
IUPAC nomenclature for organic transformations
The IUPAC Nomenclature for Transformations is a methodology for naming a chemical reaction. Traditionally a chemical reaction especially in organic chemistry is named after its inventor, the so-called name reaction, to name just a few: Knoevenagel ...
ACD/Name – Generates IUPAC, INDEX (CAS), InChi, Smiles, etc. for drawn structures in 10 languages and translates names to structures. Also available as batch tool and for Pipeline Pilot. Part of I-Lab 2.0
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