Thia-crown ether

In organic chemistry, thia-crown ethers are organosulfur compounds which are the thia analogues of crown ethers (cyclic polyethers). That is, they have a sulfur atom (sulfide linkage, −S−) in place of each oxygen atom (ether linkage, −O−) around the ring. While the parent crown ethers have the formulae (CH₂CH₂O)_n, the parent thia-crown ethers have the formulae (CH₂CH₂S)_n, where n = 3, 4, 5, 6. They have trivial names "x-ane-Sy",^{[citation needed]} 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).^[1]

Tetradentate 14-ane-S4^[2] and the hexadentate 18-ane-S6^[3] 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 ^[4].

References

^ Kueppers, H. J.; Wieghardt, K.; Nuber, B.; Weiss, J. W.; Bill, E.; Trautwein, A. X. (1987). "Crown Thioether Chemistry of Iron(II/III). Synthesis and Characterization of Low-spin Bis(1,4,7-trithiacyclononane)iron(III) and crystal structure of [Fe^II([9]aneS₃)([9]aneS₃(O))](ClO₄)₂•2NaClO₄•H₂O". Inorganic Chemistry. 26 (22): 3762–3769(8). doi:10.1021/ic00269a028.
^ Prett, V; Diaddario, L; Dockal, E; Corfield, P; Ceccarelli, C; Glick, M; Ochrymowycz, L. A.; Rorabacher, D. B. (1983). "Ring size effects on the structure of macrocyclic ligand complexes: copper(II) complexes with 12–16-membered cyclic tetrathia ethers". Inorganic Chemistry. 22 (24): 3661–3670. doi:10.1021/ic00166a033.
^ Shaw, J; Wolowska, J; Collison, D; Howard, J; McInnes, E; McMaster, J; Blake, A; Wilson, C; Schroeder, M (2006). "Redox Non-innocence of Thioether Macrocycles: Elucidation of the Electronic Structures of Mononuclear Complexes of Gold(II) and Silver(II)". Journal of the American Chemical Society. 128 (42): 13827–13839. doi:10.1021/ja0636439. PMID 17044711.
^ 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

[1] Kueppers, H. J.; Wieghardt, K.; Nuber, B.; Weiss, J. W.; Bill, E.; Trautwein, A. X. (1987). "Crown Thioether Chemistry of Iron(II/III). Synthesis and Characterization of Low-spin Bis(1,4,7-trithiacyclononane)iron(III) and crystal structure of [Fe^II([9]aneS₃)([9]aneS₃(O))](ClO₄)₂•2NaClO₄•H₂O". Inorganic Chemistry. 26 (22): 3762–3769(8). doi:10.1021/ic00269a028.

[2] Prett, V; Diaddario, L; Dockal, E; Corfield, P; Ceccarelli, C; Glick, M; Ochrymowycz, L. A.; Rorabacher, D. B. (1983). "Ring size effects on the structure of macrocyclic ligand complexes: copper(II) complexes with 12–16-membered cyclic tetrathia ethers". Inorganic Chemistry. 22 (24): 3661–3670. doi:10.1021/ic00166a033.

[3] Shaw, J; Wolowska, J; Collison, D; Howard, J; McInnes, E; McMaster, J; Blake, A; Wilson, C; Schroeder, M (2006). "Redox Non-innocence of Thioether Macrocycles: Elucidation of the Electronic Structures of Mononuclear Complexes of Gold(II) and Silver(II)". Journal of the American Chemical Society. 128 (42): 13827–13839. doi:10.1021/ja0636439. PMID 17044711.

[4] 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

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