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硫氰酸盐

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硫氰酸盐
IUPAC名
Cyanosulfanide
别名
  • Rhodanide
  • Sulfocyanate
  • Sulphocyanate
  • Thiocyanide
识别
CAS号 302-04-5  ☒N
PubChem 9322
ChemSpider 8961
SMILES
 
  • [S-]C#N
InChI
 
  • 1/CHNS/c2-1-3/h3H/p-1
InChIKey ZMZDMBWJUHKJPS-REWHXWOFAX
ChEBI 18022
IUPHAR配体 4529
性质
化学式 CNS
摩尔质量 58.08 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

硫氰酸盐硫氰酸根离子SCN所成的盐,常见的包括无色的硫氰酸钾硫氰酸钠硫氰酸铵硫氰酸汞

硫氰酸酯指含有SCN官能团的有机化合物

硫氰酸根离子与氰酸根离子[OCN]同类,只是氧原子被原子替代。[SCN]卤离子相似之处很多,是拟卤离子之一。

硫氰酸盐可由硫代硫酸盐氰化物反应制备:

磺基转移酶硫氰酸酶英语thiosulfate sulfurtransferase可催化第二个反应,可能是体内氰化物解毒的机理。

Riemschneider硫代氨基甲酸酯合成涉及有机硫氰酸酯水解为硫代氨基甲酸酯的反应。

异构

硫氰酸苯酯与异硫氰酸苯酯是键合异构体

硫氰酸根存在键合异构体

  • 硫氰酸盐和硫氰酸酯中,有机基团或金属原子与硫相连:R−S−C≡N;[1]
  • 异硫氰酸盐或异硫氰酸酯中,则与氮相连:R−N=C=S。

检测Fe3+

血红色的[Fe(NCS)(H2O)5]2+

溶液中,Fe3+会与[SCN]反应生成血红色的[Fe(SCN)(H2O)5]2+,可用于检验三价铁离子,有些电影中也用该法制作假血英语theatrical blood

Fe3+ + n SCN- → [Fe(SCN)n]3-n

药理学

硫氰酸盐[2]乳过氧化酶英语lactoperoxidase合成次硫氰酸盐英语hypothiocyanite时扮演重要角色[3][4][5]。因此当人体缺乏硫氰酸盐时[6](如囊肿性纤维化),会导致人体免疫功能下降[7][8]

硫氰酸盐也会竞争性抑制甲状腺的钠-碘共同运输蛋白英语sodium-iodide symporter(sodium-iodide symporter)[9],减少运入甲状腺滤泡的碘,进而抑制甲状腺素的合成。因此甲状腺机能低下的患者应该避免摄入含有过多硫氰酸盐的食物[10]

20世纪初期,硫氰酸盐会用于治疗高血压,但因为毒性过强而不再使用[11]。但至今仍用于高血压危症英语hypertensive emergency硝普钠,其中一个代谢物即为硫氰酸盐。硫氰酸酶英语Rhodanese会与硫代硫酸根共同作用,将硝普钠代谢为硫氰酸盐。

参见

参考资料

  1. ^ Guy, R. G. "Syntheses and Preparative Applications of Thiocyanates" in "Chemistry of Cyanates and Their Derivatives," vol II. Patai, S., (Editor), John Wiley, 1977. New York
  2. ^ Pedemonte, N.; Caci, E.; Sondo, E.; Caputo, A.; Rhoden, K.; Pfeffer, U.; di Candia, M.; Bandettini, R.; Ravazzolo, R.; Zegarra-Moran, O.; Galietta, L. J. Thiocyanate Transport in Resting and IL-4-Stimulated Human Bronchial Epithelial Cells: Role of Pendrin and Anion Channels. Journal of Immunology. 2007, 178 (8): 5144–5153. PMID 17404297. doi:10.4049/jimmunol.178.8.5144. 
  3. ^ Conner, G. E.; Wijkstrom-Frei, C.; Randell, S. H.; Fernandez, V. E.; Salathe, M. The Lactoperoxidase System Links Anion Transport to Host Defense in Cystic Fibrosis. FEBS Letters. 2007, 581 (2): 271–278. PMC 1851694可免费查阅. PMID 17204267. doi:10.1016/j.febslet.2006.12.025. 
  4. ^ White, W. E.; Pruitt, K. M.; Mansson-Rahemtulla, B. Peroxidase-Thiocyanate-Peroxide Antibacterial System Does not Damage DNA. Antimicrobial Agents and Chemotherapy. 1983, 23 (2): 267–272. PMC 186035可免费查阅. PMID 6340603. doi:10.1128/aac.23.2.267. 
  5. ^ Thomas, E. L.; Aune, T. M. Lactoperoxidase, Peroxide, Thiocyanate Antimicrobial System: Correlation of Sulfhydryl Oxidation with Antimicrobial Action. Infection and Immunity. 1978, 20 (2): 456–463. PMC 421877可免费查阅. PMID 352945. 
  6. ^ Minarowski, Ł.; Sands, D.; Minarowska, A.; Karwowska, A.; Sulewska, A.; Gacko, M.; Chyczewska, E. Thiocyanate concentration in saliva of cystic fibrosis patients (PDF). Folia Histochemica et Cytobiologica. 2008, 46 (2): 245–246. PMID 18519245. doi:10.2478/v10042-008-0037-0. [永久失效链接]
  7. ^ Moskwa, P.; Lorentzen, D.; Excoffon, K. J.; Zabner, J.; McCray, P. B. Jr.; Nauseef, W. M.; Dupuy, C.; Bánfi, B. A Novel Host Defense System of Airways is Defective in Cystic Fibrosis. American Journal of Respiratory and Critical Care Medicine. 2007, 175 (2): 174–183. PMC 2720149可免费查阅. PMID 17082494. doi:10.1164/rccm.200607-1029OC. 
  8. ^ Xu, Y.; Szép, S.; Lu, Z.; Szep; Lu. The antioxidant role of thiocyanate in the pathogenesis of cystic fibrosis and other inflammation-related diseases. Proceedings of the National Academy of Sciences of the United States of America. 2009, 106 (48): 20515–20519. Bibcode:2009PNAS..10620515X. PMC 2777967可免费查阅. PMID 19918082. doi:10.1073/pnas.0911412106. 
  9. ^ Braverman L. E.; He X.; Pino S.; et al. The effect of perchlorate, thiocyanate, and nitrate on thyroid function in workers exposed to perchlorate long-term. J Clin Endocrinol Metab. 2005, 90 (2): 700–706 [2019-04-07]. PMID 15572417. doi:10.1210/jc.2004-1821. (原始内容存档于2013-05-02). 
  10. ^ Hypothyroidism. umm.edu. University of Maryland Medical Center. [3 December 2014]. (原始内容存档于2018-03-09). 
  11. ^ Warren F. Gorman; Emanuel Messinger; And Morris Herman. Toxicity of Thiocyanates Used in Treatment of Hypertension. Ann Intern Med. 1949, 30 (5): 1054–1059. doi:10.7326/0003-4819-30-5-1054. 
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硫氰酸盐
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