thia-crown ether
{{short description|Ring molecules with several sulfide (–S–) groups}}
File:1,4,7-Trithiacyclononane.svg
In organic chemistry, thia-crown ethers are organosulfur compounds which are the thia analogues of crown ethers (cyclic polyethers).{{cite book |doi=10.1016/B978-008096518-5.00238-0 |chapter=Ten-membered Rings or Larger with One or More Sulfur Atoms |title=Comprehensive Heterocyclic Chemistry II |date=1996 |last1=Cooper |first1=Stephen R. |last2=Jones |first2=William B. |last3=Rawle |first3=Simon C. |pages=843–862 |isbn=978-0-08-096518-5 }} That is, they have a sulfur atom (sulfide linkage, {{chem2|\sS\s}}) in place of each oxygen atom (ether linkage, {{chem2|\sO\s}}) around the ring. While the parent crown ethers have the formulae {{chem2|(CH2CH2O)_{n} }}, the parent thia-crown ethers have the formulae {{chem2|(CH2CH2S)_{n} }}, where n = 3, 4, 5, 6. They have trivial names "x-ane-Sy",{{cn|date=November 2021}} 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 metals.
1,4,7-Trithiacyclononane (9-ane-S3) is a tridentate ligand and forms complexes with many metal ions, including those considered hard, such as copper(II) and iron(II).{{cite journal |author1=Kueppers, H. J. |author2=Wieghardt, K. |author3=Nuber, B. |author4=Weiss, J. W. |author5=Bill, E. |author6=Trautwein, A. X. | date = 1987 | title = Crown Thioether Chemistry of Iron(II/III). Synthesis and Characterization of Low-spin Bis(1,4,7-trithiacyclononane)iron(III) and crystal structure of [FeII([9]aneS3)([9]aneS3(O))](ClO4)2•2NaClO4•H2O | journal = Inorganic Chemistry | volume = 26 | issue = 22| pages = 3762–3769(8) | doi = 10.1021/ic00269a028}}
Tetradentate 14-ane-S4{{cite journal|author1=Prett, V|author2=Diaddario, L|author3=Dockal, E|author4=Corfield, P|author5=Ceccarelli, C|author6=Glick, M|author7=Ochrymowycz, L. A.|author8=Rorabacher, D. B. |date=1983|title = Ring size effects on the structure of macrocyclic ligand complexes: copper(II) complexes with 12–16-membered cyclic tetrathia ethers | journal=Inorganic Chemistry|volume=22|issue=24|pages=3661–3670 |doi=10.1021/ic00166a033}} and the hexadentate 18-ane-S6{{cite journal|author1=Shaw, J|author2=Wolowska, J|author3=Collison, D|author4=Howard, J|author5=McInnes, E|author6=McMaster, J|author7=Blake, A|author8=Wilson, C|author9=Schroeder, M |date=2006|title = Redox Non-innocence of Thioether Macrocycles: Elucidation of the Electronic Structures of Mononuclear Complexes of Gold(II) and Silver(II) | journal=Journal of the American Chemical Society|volume=128|issue=42|pages=13827–13839 |doi=10.1021/ja0636439|pmid=17044711|bibcode=2006JAChS.12813827S }} are also known. Evaluation of antibacterial activities of some thia crown ethers indicated that they can be considered as inhibitors for S. aureus methicillin resistance and P. aeruginosa. In addition, some of these compounds were screened for their antibacterial and antifungal activity on Klebsiella pneumoniae, Staphilococcus aureus, Pseudomanas aeruginosa and ''Candida albicans Seyedi, S. M.; Sadeghian, A.; Hazrathosseyni, A.; Sadeghian, H.; Sadeghian, M. (2007). "Synthesis and Biological Evaluation of Some New Thioether-Ester Crown Ethers". Phosphorus, Sulfur, and Silicon and the Related Elements. 182 (2): 265–272. doi:10.1080/10426500600917060.
Sadeghian, Ali; Mohammad Seyedi, Seyed; Sadeghian, Hamid; Hazrathoseyni, Ayla; Sadeghian, Mohammad (December 2007). "Synthesis, biological evaluation and QSAR studies of some new thioether–ester crown ethers". Journal of Sulfur Chemistry. 28 (6): 597–605. doi:10.1080/17415990701670718. ISSN 1741-5993.''
