2,2,2-cryptand
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.2.2ryptand is the
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula N(CH2CH2OCH2CH2OCH2CH2)3N. This
bicyclic In chemistry, a bicyclic molecule () is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic (all ...
molecule is the most studied member of the
cryptand In chemistry, cryptands are a family of synthetic, bicyclic and polycyclic, multidentate ligands for a variety of cations. The Nobel Prize for Chemistry in 1987 was given to Donald J. Cram, Jean-Marie Lehn, and Charles J. Pedersen for their e ...
family of
chelating agent Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These ligands are ...
s. It is a white solid. Many analogous compounds are known. Their high affinity for
alkali metal The alkali metals consist of the chemical elements lithium (Li), sodium (Na), potassium (K),The symbols Na and K for sodium and potassium are derived from their Latin names, ''natrium'' and ''kalium''; these are still the origins of the names ...
cations illustrates the advantages of "preorganization", a concept within the area of
supramolecular chemistry Supramolecular chemistry refers to the branch of chemistry concerning chemical systems composed of a discrete number of molecules. The strength of the forces responsible for spatial organization of the system range from weak intermolecular forces ...
. For the design and synthesis of .2.2ryptand,
Jean-Marie Lehn Jean-Marie Lehn (born 30 September 1939) is a French chemist. He received the Nobel Prize in Chemistry together with Donald Cram and Charles Pedersen in 1987 for his synthesis of cryptands. Lehn was an early innovator in the field of supramolec ...
shared the
Nobel Prize in Chemistry ) , image = Nobel Prize.png , alt = A golden medallion with an embossed image of a bearded man facing left in profile. To the left of the man is the text "ALFR•" then "NOBEL", and on the right, the text (smaller) "NAT•" then "M ...
. The compound was originally prepared starting with the diacylation of the diamine-diether: : H2OCH2CH2NH2sub>2 + H2OCH2COClsub>2 → H2OCH2CH2NHC(O)CH2sub>2 + 2 HCl The resulting
macrocyclic Macrocycles are often described as molecules and ions containing a ring of twelve or more atoms. Classical examples include the crown ethers, calixarenes, porphyrins, and cyclodextrins. Macrocycles describe a large, mature area of chemistry. ...
diamide is reduced by
lithium aluminium hydride Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li Al H4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic ...
. The resulting macrocyclic diamine tetraether reacts with a second equivalent of H2OCH2COClsub>2 to produce the macro''bi''cyclic diamide. This di(tertiary)amide is reduced to the diamine by
diborane Diborane(6), generally known as diborane, is the chemical compound with the formula B2H6. It is a toxic, colorless, and pyrophoric gas with a repulsively sweet odor. Diborane is a key boron compound with a variety of applications. It has attracte ...
. .2.2ryptand binds K+ as an octadentate N2O6 ligand. The resulting cation K( .2.2ryptand)+ is lipophilic.


References

{{DEFAULTSORT:Cryptand, 2.2.2- Chelating agents