每周分子 | Molecule of the Week
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每周分子：Croconate violet
Molecule of the Week: Croconate violet
Croconate violet是环状不饱和氧碳盐克酮酸盐(Croconate)家族的一员。Croconate本身是一个五元环，具有五个氧原子和2个负电荷。Croconate violet是将Croconate的两个氧原子得用二氰亚甲基取代；但Croconate violet的名字中保留了 “croconate”。
尽管具有如本文图中所示的结构，croconate violet的π电子就像所有克酮酸盐中的π电子一样，是完全离域的，这也使croconate violet具有了其分子特性。croconate violet是由美国国家标准局(美国华盛顿；现位于美国马里兰州盖瑟斯堡的国家标准和技术研究院)的Alexander J. Fatiadi所命名的，他在1977年报道了croconate violet的合成。
Fatiadi用丙二腈处理克酮酸二钾(dipotassium croconate)或其他克酮酸盐制备获得了产率为95%的croconate violet。以水为溶剂的重结晶使croconate violet晶体如其二水合物般呈深蓝色金属外观针状晶体。电子离域使该分子具有近似平面的结构。
在浓盐酸中加热croconate violet可制得中性的二羟基形式的橙色晶体，其在260-270°C分解熔化。尽管颜色不同，Fatiadi还是把这种化合物命名为"croconic acid violet"。其盐或酸溶解于水呈深紫色，该深紫色水溶液在533 nm处吸收最强。应小心处理该水溶液，因为它会弄脏皮肤。
Croconate violet染色特性的最新应用是蛋白质染色。人们正考虑用它来替代历史悠久的考马斯亮蓝染料，考马斯亮蓝染料自1963年以来一直用于蛋白质染色。Fatiadi在其原著论文中还指出croconate violet是一种电导率为2x10–4 S/cm的半导体。截至本文撰写时，尚无croconate violet危害信息的报道。
Croconate violet信息速览
【关于每周分子】
自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社 (CAS) 提供的SciFinder中的CAS REGISTRY获取“每周分子”的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至motw@acs.org推荐您感兴趣的分子吧。
Croconate violet is a member of the croconate family of salts of cyclic unsaturatedoxocarbons. Croconate itself is a five-membered ring with five oxygen atoms anda 2– charge. Croconate violet has dicyanomethylene groups in place of two ofthe oxygen atoms; but it retains the trivial name “croconate”.
Despite the structures shown, croconate violet’sπ-electrons, like those in all croconates, are completely delocalized and areresponsible for the molecules’ distinctive properties. Croconate violet wasnamed by Alexander J. Fatiadi at the US National Bureau of Standards(Washington, DC; now the National Institute of Standards and Technology,Gaithersburg, MD), who reported its synthesis in 1977.
Fatiadi prepared croconate violet in 95% yield by treating dipotassium croconate or other croconate salts with malononitrile. Recrystallization from water gave crystalline croconate violet as its dihydrate as deep blue needle-like crystals with a metallic appearance. Electron delocalization gives the molecule a nearly planar structure.
Heating croconate violet in concentrated hydrochloricacid gave the neutral dihydroxy form as orange crystals that melt withdecomposition at 260–270 °C. Despite its color, Fatiadi named this compound“croconic acid violet”. Dissolving thesalt or the acid in water gives a deep violet solution with an intenseabsorption maximum at 533 nm. The aqueous solution should be handled carefullybecause it stains the skin.
A recent use of the dyeing properties of croconateviolet is protein staining. It is being considered as a replacement for thevenerable Coomassie brilliant blue wool dyes, which have been used for protein staining since 1963. In his originalpaper, Fatiadi also noted that croconate violet is a semiconductor with anelectrical conductivity of 2 x 10–4 S/cm. As of this writing, no hazard information for croconateviolet was available.
Xylanfast facts
About Molecule of the Week
MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using SciFinder. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.
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