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弗氏盐

行進 31, 2023

弗氏盐是一种无机化合物，化学式 (K4[ON(SO3)2]2)，有时写作 (K2[NO(SO3)2])。它是一种亮黄棕色固体，但水溶液是亮紫色的。[1][2] 相关的钠盐亚硝基二磺酸钠（简称NDS，化学式 Na2ON(SO3)2，CAS号 29554-37-8）也被称为弗氏盐。[3]

弗氏盐
IUPAC名
Potassium nitrosodisulfonate
别名 亚硝基二磺酸钾
识别
CAS号 14293-70-0  N
PubChem 3032624
ChemSpider 2297553
SMILES
性质
化学式 K2NO(SO3)2
摩尔质量 268.33 (钾盐) g·mol⁻¹
危险性
警示术语 R：R14 R20/21/22
安全术语 S：S36
H-术语 H260, H302, H312, H332
P-术语 P223, P231+232, P280, P301+312, P302+352+312, P304+340+312
主要危害 有害 (Xn)
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

应用

弗氏盐作为一种长寿命的自由基，是电子自旋共振 (EPR) 的标准。其强烈的EPR谱线由三条等强度的线主导，间距约为 13 G（1.3 mT）。[4][5][6]

弗氏盐可用于某些氧化反应，例如某些苯胺或苯酚的氧化。[7][8][9][10][11]它也允许肽和基于肽的水凝胶（英语：Hydrogel）的聚合和交联。[12][13]

它还可以用作研究中过氧自由基的模型，以研究各种天然产品中抗氧化作用的机制。[14]

制备

弗氏盐可以由羟胺二磺酸开始制备而成。氧化它的共轭碱可以得到紫色的双阴离子：

HON(SO3H)2 → [HON(SO3)2]2− + 2 H+
2 [HON(SO3)2]2− + PbO2 → 2 [ON(SO3)2]2− + PbO + H2O

羟胺二磺酸盐则是由亚硝酸盐和亚硫酸氢盐反应而成的。氧化反应通常是在低温下进行的，可以通过化学方法或电解达成。[3][2]

其它制备方法：

HNO2 + 2 HSO−
3 → HON(SO
3)2−
2 + H2O
3 HON(SO
3)2−
2 + MnO−
4 + H+ → 3 ON(SO
3)2−
2 + MnO2 + 2 H2O
2 ON(SO
3)2−
2 + 4 K+ → K4[ON(SO3)2]2

历史

弗氏盐是在1845年由埃德蒙·弗雷米 (1814–1894)发现的。[15]

参考资料

  1. ^ Greenwood, Norman Neill; Earnshaw, Alan. Chemistry of the elements. 2016. ISBN 978-0-7506-3365-9. OCLC 1040112384 （英语）. 
  2. ^ 2.0 2.1 (PDF). tripod.com. [2021-12-03]. （原始内容 (PDF)存档于2010-09-23）. 
  3. ^ 3.0 3.1 Wehrli PA, Pigott F. Oxidation with the nitrosodisulfonate radical. I. Preparation and use of sodium nitrosodisulfonate: trimethyl-p-benzoquinone. Organic Syntheses. 1972, 52: 83. doi:10.15227/orgsyn.052.0083. 
  4. ^ Wertz JE, Bolton JR. Electron Spin Resonance: Elementary Theory and Practical Applications. New York: McGraw-Hill. 1972. ISBN 978-0-07-069454-5.  See page 463 for information on intensity measurements and page 86 for an EPR spectrum of Frémy's salt.
  5. ^ Colacicchi S, Carnicelli V, Gualtieri G, Di Giulio A. EPR study of Frémy's salt nitroxide reduction by ascorbic acid; influence of bulk pH values. Res. Chem. Intermed. 2000, 26 (9): 885–896. S2CID 98775951. doi:10.1163/156856700X00372. 
  6. ^ Zielonka J, Zhao H, Xu Y, Kalyanaraman B. Mechanistic similarities between oxidation of hydroethidine by Frémy's salt and superoxide: stopped-flow optical and EPR studies. Free Radical Biology & Medicine. October 2005, 39 (7): 853–863. PMID 16140206. doi:10.1016/j.freeradbiomed.2005.05.001. 
  7. ^ Zimmer H, Lankin DC, Horgan SW. Oxidations with potassium nitrosodisulfonate (Frémy's radical). Teuber reaction.. Chemical Reviews. 1971, 71 (2): 229–246. doi:10.1021/cr60270a005. 
  8. ^ Islam I, Skibo EB, Dorr RT, Alberts DS. Structure-activity studies of antitumor agents based on pyrrolo[1,2-a]benzimidazoles: new reductive alkylating DNA cleaving agents. Journal of Medicinal Chemistry. October 1991, 34 (10): 2954–2961. PMID 1920349. doi:10.1021/jm00114a003. 
  9. ^ Teuber HJ, Benz S. Reaktionen mit Nitrosodisulfonat, XXXVI. Chinolin-chinone-(5.6) aus 5-Hydroxy-chinolinen. Chem. Ber. 1967, 100 (9): 2918–2929. doi:10.1002/cber.19671000916 （德语）. [失效連結]
  10. ^ Teuber HJ. Use of dipotassium nitrosodisulfonate (Frémy's salt): 4,5-dimethyl-o-benzoquinone. Org. Synth. 1972, 52: 88. doi:10.15227/orgsyn.052.0088. 
  11. ^ Xue W, Warshawsky D, Rance M, Jayasimhulu K. A metabolic activation mechanism of 7H-dibenzo[c,g]carbozole via o-quinone. Part 1: synthesis of 7H-dibenzo[c,g]carbozole-3,4-dione and reactions with nucleophiles. Polycyclic Aromatic Compounds. 2002, 22 (3–4): 295–300. S2CID 95507636. doi:10.1080/10406630290026957. 
  12. ^ Wilchek M, Miron T. Mussel-inspired new approach for polymerization and cross-linking of peptides and proteins containing tyrosines by Frémy's salt oxidation. Bioconjugate Chemistry. March 2015, 26 (3): 502–510. PMID 25692389. doi:10.1021/bc5006152. 
  13. ^ Fichman G, Schneider JP. Utilizing Frémy's Salt to Increase the Mechanical Rigidity of Supramolecular Peptide-Based Gel Networks. Frontiers in Bioengineering and Biotechnology. 2021, 8: 594258. PMC 7813677  . PMID 33469530. doi:10.3389/fbioe.2020.594258   （英语）. 
  14. ^ Liu ZL, Han ZX, Chen P, Liu YC. Stopped-flow ESR study on the reactivity of vitamin E, vitamin C and its lipophilic derivatives towards Frémy's salt in micellar systems. Chemistry and Physics of Lipids. November 1990, 56 (1): 73–80. PMID 1965427. doi:10.1016/0009-3084(90)90090-E. 
  15. ^ 参见：
    • Frémy, E. (1845) "Sur un nouvelle série d'acides formés d'oxygène, de soufre, d'hydrogène et de d'azote" （页面存档备份，存于互联网档案馆） (On a new series of acids formed from oxygen, sulfur, hydrogen, and nitrogen), Annales de Chimie et de Physique, 3rd series, 15 : 408-488. Frémy's salt appears on p. 447 （页面存档备份，存于互联网档案馆）, where it's called "sulfazidate de potasse".
    • Frémy, E. (1845) "Sur un nouvelle série d'acides formés d'oxygène, de soufre, d'hydrogène et de d'azote" （页面存档备份，存于互联网档案馆） (On a new series of acids formed from oxygen, sulfur, hydrogen, and nitrogen), Comptes rendus, 21 : 218–226. This is a condensed version of the article that appeared in Annales de Chimie et de Physique.
    • "Séances académiques," L'Institut, no. 604, 23 July 1845, pp. 265–266. （页面存档备份，存于互联网档案馆）
    • "Séances académiques," L'Institut, no. 619, 12 November 1845, pp. 393. （页面存档备份，存于互联网档案馆） Here a committee of the French Academy of Sciences reviewed Frémy's findings.
    • Edward Divers and Tamemasa Haga (1900) "Identification and constitution of Frémy's sulphazotised salts of potassium," （页面存档备份，存于互联网档案馆） Journal of the Chemical Society, Transactions, 77 : 440-446. doi:10.1039/CT9007700440 Here, correct formulae for Frémy's salts are presented. On p. 445 （页面存档备份，存于互联网档案馆）, the salt that Frémy called sulfazidate is identified as ON(SO3K)2.

扩展阅读

  • Morey J. Undergraduate Experiments with a Long-Lived Radical (Frémy's salt): Synthesis of 1,4-Benzoquinones by Degradative Oxidation of p-Hydroxybenzyl Alcohols. J. Chem. Educ. 1988, 65 (7): 627–629. Bibcode:1988JChEd..65..627M. doi:10.1021/ed065p627. 

行進 31, 2023
弗氏盐, 是一种无机化合物, 化学式, 有时写作, 它是一种亮黄棕色固体, 但水溶液是亮紫色的, 相关的钠盐亚硝基二磺酸钠, 简称nds, 化学式, na2on, cas号, 29554, 也被称为, iupac名potassium, nitrosodisulfonate别名, 亚硝基二磺酸钾识别cas号, 14293, npubchem, 3032624chemspider, 2297553smiles, 性质化学式, k2no, 2摩尔质量, 钾盐, 危险性警示术语, 22安全术语, s36h, 术语, h26. 弗氏盐是一种无机化合物 化学式 K4 ON SO3 2 2 有时写作 K2 NO SO3 2 它是一种亮黄棕色固体 但水溶液是亮紫色的 1 2 相关的钠盐亚硝基二磺酸钠 简称NDS 化学式 Na2ON SO3 2 CAS号 29554 37 8 也被称为弗氏盐 3 弗氏盐IUPAC名Potassium nitrosodisulfonate别名 亚硝基二磺酸钾识别CAS号 14293 70 0 NPubChem 3032624ChemSpider 2297553SMILES N O S O O O S O O O K K 性质化学式 K2NO SO3 2摩尔质量 268 33 钾盐 g mol 危险性警示术语 R R14 R20 21 22安全术语 S S36H 术语 H260 H302 H312 H332P 术语 P223 P231 232 P280 P301 312 P302 352 312 P304 340 312主要危害 有害 Xn 若非注明 所有数据均出自标准状态 25 100 kPa 下 目录 1 应用 2 制备 3 历史 4 参考资料 5 扩展阅读应用 编辑弗氏盐作为一种长寿命的自由基 是电子自旋共振 EPR 的标准 其强烈的EPR谱线由三条等强度的线主导 间距约为 13 G 1 3 mT 4 5 6 弗氏盐可用于某些氧化反应 例如某些苯胺或苯酚的氧化 7 8 9 10 11 它也允许肽和基于肽的水凝胶 英语 Hydrogel 的聚合和交联 12 13 它还可以用作研究中过氧自由基的模型 以研究各种天然产品中抗氧化作用的机制 14 制备 编辑弗氏盐可以由羟胺二磺酸开始制备而成 氧化它的共轭碱可以得到紫色的双阴离子 HON SO3H 2 HON SO3 2 2 2 H 2 HON SO3 2 2 PbO2 2 ON SO3 2 2 PbO H2O羟胺二磺酸盐则是由亚硝酸盐和亚硫酸氢盐反应而成的 氧化反应通常是在低温下进行的 可以通过化学方法或电解达成 3 2 其它制备方法 HNO2 2 HSO 3 HON SO3 2 2 H2O 3 HON SO3 2 2 MnO 4 H 3 ON SO3 2 2 MnO2 2 H2O 2 ON SO3 2 2 4 K K4 ON SO3 2 2历史 编辑弗氏盐是在1845年由埃德蒙 弗雷米 1814 1894 发现的 15 参考资料 编辑 Greenwood Norman Neill Earnshaw Alan Chemistry of the elements 2016 ISBN 978 0 7506 3365 9 OCLC 1040112384 英语 2 0 2 1 Synthesis and Characterization of Potassium Nitrosodisulfonate Fremy s Salt PDF tripod com 2021 12 03 原始内容 PDF 存档于2010 09 23 3 0 3 1 Wehrli PA Pigott F Oxidation with the nitrosodisulfonate radical I Preparation and use of sodium nitrosodisulfonate trimethyl p benzoquinone Organic Syntheses 1972 52 83 doi 10 15227 orgsyn 052 0083 Wertz JE Bolton JR Electron Spin Resonance Elementary Theory and Practical Applications New York McGraw Hill 1972 ISBN 978 0 07 069454 5 See page 463 for information on intensity measurements and page 86 for an EPR spectrum of Fremy s salt Colacicchi S Carnicelli V Gualtieri G Di Giulio A EPR study of Fremy s salt nitroxide reduction by ascorbic acid influence of bulk pH values Res Chem Intermed 2000 26 9 885 896 S2CID 98775951 doi 10 1163 156856700X00372 Zielonka J Zhao H Xu Y Kalyanaraman B Mechanistic similarities between oxidation of hydroethidine by Fremy s salt and superoxide stopped flow optical and EPR studies Free Radical Biology amp Medicine October 2005 39 7 853 863 PMID 16140206 doi 10 1016 j freeradbiomed 2005 05 001 Zimmer H Lankin DC Horgan SW Oxidations with potassium nitrosodisulfonate Fremy s radical Teuber reaction Chemical Reviews 1971 71 2 229 246 doi 10 1021 cr60270a005 Islam I Skibo EB Dorr RT Alberts DS Structure activity studies of antitumor agents based on pyrrolo 1 2 a benzimidazoles new reductive alkylating DNA cleaving agents Journal of Medicinal Chemistry October 1991 34 10 2954 2961 PMID 1920349 doi 10 1021 jm00114a003 Teuber HJ Benz S Reaktionen mit Nitrosodisulfonat XXXVI Chinolin chinone 5 6 aus 5 Hydroxy chinolinen Chem Ber 1967 100 9 2918 2929 doi 10 1002 cber 19671000916 德语 失效連結 Teuber HJ Use of dipotassium nitrosodisulfonate Fremy s salt 4 5 dimethyl o benzoquinone Org Synth 1972 52 88 doi 10 15227 orgsyn 052 0088 Xue W Warshawsky D Rance M Jayasimhulu K A metabolic activation mechanism of 7H dibenzo c g carbozole via o quinone Part 1 synthesis of 7H dibenzo c g carbozole 3 4 dione and reactions with nucleophiles Polycyclic Aromatic Compounds 2002 22 3 4 295 300 S2CID 95507636 doi 10 1080 10406630290026957 Wilchek M Miron T Mussel inspired new approach for polymerization and cross linking of peptides and proteins containing tyrosines by Fremy s salt oxidation Bioconjugate Chemistry March 2015 26 3 502 510 PMID 25692389 doi 10 1021 bc5006152 Fichman G Schneider JP Utilizing Fremy s Salt to Increase the Mechanical Rigidity of Supramolecular Peptide Based Gel Networks Frontiers in Bioengineering and Biotechnology 2021 8 594258 PMC 7813677 PMID 33469530 doi 10 3389 fbioe 2020 594258 英语 Liu ZL Han ZX Chen P Liu YC Stopped flow ESR study on the reactivity of vitamin E vitamin C and its lipophilic derivatives towards Fremy s salt in micellar systems Chemistry and Physics of Lipids November 1990 56 1 73 80 PMID 1965427 doi 10 1016 0009 3084 90 90090 E 参见 Fremy E 1845 Sur un nouvelle serie d acides formes d oxygene de soufre d hydrogene et de d azote 页面存档备份 存于互联网档案馆 On a new series of acids formed from oxygen sulfur hydrogen and nitrogen Annales de Chimie et de Physique 3rd series 15 408 488 Fremy s salt appears on p 447 页面存档备份 存于互联网档案馆 where it s called sulfazidate de potasse Fremy E 1845 Sur un nouvelle serie d acides formes d oxygene de soufre d hydrogene et de d azote 页面存档备份 存于互联网档案馆 On a new series of acids formed from oxygen sulfur hydrogen and nitrogen Comptes rendus 21 218 226 This is a condensed version of the article that appeared in Annales de Chimie et de Physique Seances academiques L Institut no 604 23 July 1845 pp 265 266 页面存档备份 存于互联网档案馆 Seances academiques L Institut no 619 12 November 1845 pp 393 页面存档备份 存于互联网档案馆 Here a committee of the French Academy of Sciences reviewed Fremy s findings Edward Divers and Tamemasa Haga 1900 Identification and constitution of Fremy s sulphazotised salts of potassium 页面存档备份 存于互联网档案馆 Journal of the Chemical Society Transactions 77 440 446 doi 10 1039 CT9007700440 Here correct formulae for Fremy s salts are presented On p 445 页面存档备份 存于互联网档案馆 the salt that Fremy called sulfazidate is identified as ON SO3K 2 扩展阅读 编辑Morey J Undergraduate Experiments with a Long Lived Radical Fremy s salt Synthesis of 1 4 Benzoquinones by Degradative Oxidation of p Hydroxybenzyl Alcohols J Chem Educ 1988 65 7 627 629 Bibcode 1988JChEd 65 627M doi 10 1021 ed065p627 取自 https zh wikipedia org w index php title 弗氏盐 amp oldid 72352672, 维基百科，wiki，书籍，书籍，图书馆，

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