Atranes are a class of tricyclic

molecule A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...

s with three five-membered rings. It is a

heterocyclic A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

structure similar to the

propellane In organic chemistry, propellane is any member of a class of polycyclic compound, polycyclic hydrocarbons, whose carbon skeleton consists of three rings of carbon atoms sharing a common carbon–carbon bond, carbon–carbon covalent bond. The co ...

s. It has a

transannular In organic chemistry, annulation (; occasionally annelation) is a chemical reaction in which a new ring is constructed on a molecule. : Examples are the Robinson annulation, Danheiser annulation and certain cycloadditions. Annular molecules ar ...

dative bond In coordination chemistry, a coordinate covalent bond, also known as a dative bond, dipolar bond, or coordinate bond is a kind of two-center, two-electron covalent bond in which the two electrons derive from the same atom. The bonding of metal io ...

from a

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. ...

at one bridgehead to a

Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any ...

ic atom such as silicon or boron at the other bridgehead.Voronkov, Mikhail G.; Baryshok, Viktor P. "Atranes - a new generation of biologically active substances" (in Russian) Vestnik Rossiiskoi Akademii Nauk 2010, volume 80, 985-992. The name "atrane" was first proposed by .

Nomenclature

Various atranes are named depending on the central

element 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 o ...

, e.g. "silatrane" (E =

silicon Silicon is a chemical element; it has symbol Si and atomic number 14. It is a hard, brittle crystalline solid with a blue-grey metallic lustre, and is a tetravalent metalloid (sometimes considered a non-metal) and semiconductor. It is a membe ...

); "boratrane" (E =

boron Boron is a chemical element; it has symbol B and atomic number 5. In its crystalline form it is a brittle, dark, lustrous metalloid; in its amorphous form it is a brown powder. As the lightest element of the boron group it has three ...

); "phosphatrane" (E =

phosphorus Phosphorus is a chemical element; it has Chemical symbol, symbol P and atomic number 15. All elemental forms of phosphorus are highly Reactivity (chemistry), reactive and are therefore never found in nature. They can nevertheless be prepared ar ...

), etc. It is also proposed that when Y = nitrogen, the prefix "aza" be inserted before ''element'' + "atrane" (azasilatrane, for example) because atranes wherein E = silicon and Y =

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 ...

have been referred to as just "silatranes".

Structure and properties

Silatranes exhibit unusual properties, as the transannular coordinate bond in atranes can be stretched (quasiatranes) and even broken (proatranes). The strength (and multiplicity) of the central bond depends on the stereoelectronic properties of the surrounding ligands, the

electronegativity Electronegativity, symbolized as , is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. An atom's electronegativity is affected by both its atomic number and the ...

of the participating atoms, and the size of the rings. A strong driving force for the formation of the central bond is relief of

ring strain In organic chemistry, ring strain is a type of instability that exists when bonds in a molecule form angles that are abnormal. Strain is most commonly discussed for small rings such as cyclopropanes and cyclobutanes, whose internal angles ar ...

from the otherwise-formed 8-membered rings. Atranes exhibit biological activity in which the coordination of nitrogen to

silane Silane (Silicane) is an inorganic compound with chemical formula . It is a colorless, pyrophoric gas with a sharp, repulsive, pungent smell, somewhat similar to that of acetic acid. Silane is of practical interest as a precursor to elemental ...

plays an important role. Some derivatives such as phenylsilatrane are highly toxic. upright=1.5, center, Protonation of Verkade base gives an atrane. Proazaphosphatrane is a very strong non-

ion 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 convent ...

ic base and is utilized in various types of

organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...

synthesis Synthesis or synthesize may refer to: Science Chemistry and biochemistry *Chemical synthesis, the execution of chemical reactions to form a more complex molecule from chemical precursors **Organic synthesis, the chemical synthesis of organi ...

as an efficient

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

References

{{commons category, lcfirst=yes Heterocyclic compounds

Nomenclature

Structure and properties

See also

References