organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...

, a 1,3-dipolar compound or 1,3-dipole is a

dipolar compound In organic chemistry, a dipolar compound or simply dipole is an electrically neutral molecule carrying a positive and a negative charge in at least one canonical description. In most dipolar compounds the charges are Delocalized electron, delocali ...

with

delocalized electron In chemistry, delocalized electrons are electrons in a molecule, ion or solid metal that are not associated with a single atom or a covalent bond.IUPAC Gold Boo''delocalization''/ref> The term delocalization is general and can have slightly dif ...

s and a separation of charge over three

atom Atoms are the basic particles of the chemical elements. An atom consists of a atomic nucleus, nucleus of protons and generally neutrons, surrounded by an electromagnetically bound swarm of electrons. The chemical elements are distinguished fr ...

s. They are reactants in 1,3-dipolar cycloadditions. The dipole has at least one

resonance structure In chemistry, resonance, also called mesomerism, is a way of describing bonding in certain molecules or polyatomic ions by the combination of several contributing structures (or ''forms'', also variously known as ''resonance structures'' or '' ...

with positive and negative charges having a 1,3 relationship which can generally be denoted as , where a may be a

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

oxygen Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

, b may be nitrogen or oxygen, and c may be a carbon, oxygen or nitrogen. Known 1,3-dipoles are: *

Azide In chemistry, azide (, ) is a linear, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant ...

s () *

Ozone Ozone () (or trioxygen) is an Inorganic compound, inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , break ...

() *

Nitro compound In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nit ...

s () *

Diazo In organic chemistry, the diazo group is an organic moiety consisting of two linked nitrogen atoms at the terminal position. Overall charge-neutral organic compounds containing the diazo group bound to a carbon atom are called diazo compounds ...

compounds () * Some

oxide An oxide () is a chemical compound containing at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion (anion bearing a net charge of −2) of oxygen, an O2− ion with oxygen in the oxidation st ...

s ** Azoxide compounds (RN(O)NR) ** Carbonyl oxides ( Criegee zwitterions)Li, Jie Jack
''Criegee mechanism of ozonolysis''
Book: Name Reactions. 2006, 173-174, ** Nitrile oxides () **

Nitrous oxide Nitrous oxide (dinitrogen oxide or dinitrogen monoxide), commonly known as laughing gas, nitrous, or factitious air, among others, is a chemical compound, an Nitrogen oxide, oxide of nitrogen with the Chemical formula, formula . At room te ...

() ** Nitrones () Carbonyl oxide-resonance

* Some

imine In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bon ...

s: ** Azomethine imine **

Nitrilimine Nitrilimines or nitrile amides are a class of organic compounds sharing a common functional group with the general structure corresponding to the conjugate base of an amine bonded to the N-terminus of a nitrile. The dominant structure for the paren ...

s (, analogous to nitrile oxide) ** Carbonyl imines * Some

ylide An ylide () or ylid () is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both ...

s ** Azomethine ylide ** Nitrile ylide () ** Carbonyl ylide ** Thiosulfines ()

References

{{Reflist Organic chemistry