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

, thia-crown ethers are

organosulfur compound Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfu ...

s which are the ''

thia The thumbnail crab, ''Thia scutellata'', is a species of decapods, in the family of thiidae, whose carapace resembles a human thumbnail, a dense fringe of long hairs distinctly notched around the edge. Pale pink in colour with red to brown mar ...

'' analogues of

crown ether In organic chemistry, crown ethers are cyclic chemical compounds that consist of a ring containing several ether groups (). The most common crown ethers are cyclic oligomers of ethylene oxide, the repeating unit being ethyleneoxy, i.e., . Impor ...

s (cyclic polyethers). That is, they have a

sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...

atom (

sulfide Sulfide (British English also sulphide) is an inorganic anion of sulfur with the chemical formula S2− or a compound containing one or more S2− ions. Solutions of sulfide salts are corrosive. ''Sulfide'' also refers to chemical compounds lar ...

linkage, ) in place of each

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...

atom (

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

linkage, ) around the

ring Ring may refer to: * Ring (jewellery), a round band, usually made of metal, worn as ornamental jewelry * To make a sound with a bell, and the sound made by a bell :(hence) to initiate a telephone connection Arts, entertainment and media Film and ...

. While the parent crown ethers have the formulae , the parent ''thia''-crown ethers have the formulae , where ''n'' = 3, 4, 5, 6. They have trivial names "''x''-ane-S''y''", where ''x'' and ''y'' are the number of atoms in the ring and the number of those atoms that are sulfur, respectively. Thia-crown ethers exhibit affinities for

transition metal In chemistry, a transition metal (or transition element) is a chemical element in the d-block of the periodic table (groups 3 to 12), though the elements of group 12 (and less often group 3) are sometimes excluded. They are the elements that can ...

s. 1,4,7-Trithiacyclononane (9-ane-S3) is a tridentate ligand and forms complexes with many metal ions, including those considered

hard Hard may refer to: * Hardness, resistance of physical materials to deformation or fracture * Hard water, water with high mineral content Arts and entertainment * ''Hard'' (TV series), a French TV series * Hard (band), a Hungarian hard rock supe ...

, such as

copper Copper is a chemical element with the symbol Cu (from la, cuprum) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkis ...

(II) and

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 f ...

(II).

Tetradentate In chemistry, tetradentate ligands are ligands that bind four donor atoms to a central atom to form a coordination complex. This number of donor atoms that bind is called denticity and is a method of classifying ligands. Tetradentate ligands ar ...

14-ane-S4 and the

hexadentate A hexadentate ligand in coordination chemistry is a ligand that combines with a central metal atom with six bonds. One example of a hexadentate ligand that can form complexes with soft metal ions is TPEN. A commercially important hexadentate liga ...

18-ane-S6 are also known.

References

{{reflist Sulfur heterocycles Thioethers Chelating agents Macrocycles