四乙基氯化铵,简称TEAC,是一种季铵盐,化学式 (C2H5)4N+Cl−,有时写作Et4N+Cl−。它是吸湿性的无色晶体。在药理学和生理学研究中,它已被用作四乙基铵阳离子的来源,也用于有机化学合成。
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TEAC可以由三乙胺和氯乙烷反应而成。[2]
TEAC有两种稳定的水合物,分别是一水合物和四水合物。[3]一水合物TEAC.H2O 的晶体结构已确定,[4] 四水合物TEAC.4H2O也是如此。[5]
Harmon和Gabriele提供了制备大量TEAC.H2O晶体的详细信息,他们对该化合物和相关化合物进行了红外光谱学研究。[6]研究人员也指出,尽管刚提纯的 TEAC.H2O 不含三乙胺盐酸盐,但加热TEAC时会通过霍夫曼消除反应产生少量的三乙胺盐酸盐。
- Cl− + H-CH2-CH2-N+Et3 → Cl-H + H2C=CH2 + Et3N
在很大程度上,TEAC的合成应用类似于四乙基溴化铵(TEAB)和四乙基碘化铵(TEAI),尽管其中一种盐在特定反应中可能比另一种更有效。举个例子,TEAC在从芳胺、硝基芳烃和一氧化碳制备二芳基脲的反应中作为助催化剂的产率比TEAB和TEAI高。[7]
在其他示例中,例如以下示例,TEAC不如TEAB或TEAI有效:
与四乙基溴化铵和四乙基碘化铵一样,TEAC已被用作许多临床和药理学研究的四乙基铵离子来源,在四乙基铵盐条目下有更详细的介绍。简而言之,TEAC的神经节阻滞特性已在临床上进行了探索。[10]虽然它现在作为药物基本上已经过时,但它仍然用于生理研究,因为它能够阻断各种组织中的 K+ 通道。[11][12]
TEAC的毒性是由四乙基铵阳离子导致的,这已被广泛研究。TEAC的急性毒性可以和四乙基溴化铵和四乙基碘化铵比较。这些数据[13]是用于比较目的,详细信息可在四乙基铵盐条目中找到。
Roose, Peter; Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut, Amines, Aliphatic, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a02_001.pub2
K. M. Harmon, J. M. Gabriele and J. Harmon (1990). "Hydrogen bonding Part 30. New IR spectra-structure correlations for tetraethylammonium, tetramethylammonium, and N,N-dimethyl-pyrrolidinium fluoride monohydrates, tetraethylammonium chloride monohydrate, and tetramethylammonium hydroxide dihydrate; evidence for a planar (H2O.F−)2 cluster". J. Mol. Struct. 216 53-62.
J. H. Loehlin and A. Kvick (1978). "Tetraethylammonium chloride monohydrate". Acta Crystallographica Section B 34 3488–3490.
Y.-S. Lam and T. C. W. Mak (1978). "Crystal data for some tetraethylammonium salt hydrates". 11 193.
Harmon, Kenneth M.; Gabriele, Julie M. Hydrogen bonding. 11. Infrared study of the water-chloride ion cluster in tetraethylammonium chloride hydrate. Inorganic Chemistry. 1981, 20 (11): 4013–4015. doi:10.1021/ic50225a087.
H. A. Dieck, R. M. Laine and R. F. Heck (1975). "Low-pressure, palladium-catalyzed N,N'-diarylurea synthesis from nitro compounds, amines, and carbon monoxide". J. Org. Chem. 40 2819–2822.
T.Yoshino et al. (1977). "Synthetic studies with carbonates. Part 6. Syntheses of 2-hydroxyethyl derivatives by reactions of ethylene carbonate with carboxylic acids or heterocycles in the presence of tetraethylammonium halides or under autocatalytic conditions". J. Chem. Soc., Perkin 1 1266–1272.
G. Saikia and P. K. Iyer (2010). "Facile C-H alkylation in water: enabling defect-free materials for optoelectronic devices". J. Org. Chem. 75 2714–2717.
G. K. Moe and W. A. Freyburger (1950). "Ganglionic blocking agents". Pharmacol. Rev. 2 61–95.
B. Hille (1967). "The selective inhibition of delayed potassium currents in nerve by tetraethylammonium ions". J. Gen. Physiol. 50 1287–1302.
C. M. Armstrong and B. Hille (1972). "The inner quaternary ammonium receptor in potassium channels of the node of Ranvier". J. Gen. Physiol. 59 388–400.
O. M. Gruhzit, R. A. Fisken and B. J. Cooper (1948). "Tetraethylammonium chloride [(C2H5)4NCl]. Acute and chronic toxicity in experimental animals". J. Pharmacol. Exp. Ther. 92 103–107.