Structural, spectroscopic and electrochemical characterizations of new 2,5-bis(phosphoranyl)-3,6-diaminoquinones

IF 1.4 4区化学 Q4 CHEMISTRY, INORGANIC & NUCLEAR

Phosphorus, Sulfur, and Silicon and the Related Elements Pub Date : 2024-09-02 DOI:10.1080/10426507.2024.2409435

Madison E. Lear , Connor P. McLoughlin , Alea Ha , Joshua M. Paul , Amanda N. Graveson , Nathan A. Phan , Timothy J. Dobson , Natalie C. Cawker , Edward J. Valente , Eugenijus Urnezius

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引用次数: 0

Abstract

Cu(II) catalyzed open air reactions of 2,5-bis(-P(O)R₂))-3,6-dichloro-hydroquinones (R = Ph or iPr) with selected primary amines or ammonia proceeded with oxidation of the hydroquinone ring and substitution of chlorines by the amino groups. The products of these reactions were 2,5-bis(-P(O)R₂))-3,6-di(-NHR’)-quinones (1a, R = Ph, R′ = Cy; 1b, R = iPr, R′ = Cy; 2a, R = Ph, R′ = –CH(CH₂OH)₂; 2b, R = iPr, R′ = –CH(CH₂OH)₂; 3a, R = Ph, R′ = –CH₂CH(OH)CH₂OH; 3b, R = iPr, R′ = CH₂CH(OH)CH₂OH; 4a (R = Ph, R′ = H; 4b, R = iPr, R′ = H). They were isolated as bright orange or yellow solids in moderate/good yields. The compounds were characterized by multinuclear (¹H,¹³C,³¹P) NMR, FT-IR, UV–Vis, high resolution mass-spectrometry, and cyclic voltammetry. Compounds 1b, 2a, 3a and 4a,b were also characterized by single crystal X-ray diffraction methods.

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新型2,5-二（磷酰）-3,6-二氨基醌的结构、光谱和电化学表征

铜（II）催化2,5-二（-P(O)R2）)-3,6-二氯对苯二酚（R = Ph或iPr）与选定的伯胺或氨的露天反应，进行对苯二酚环氧化和氯被氨基取代。这些反应的产物是2,5-二（-P(O)R2）)-3,6-二(-NHR ')-醌(1a, R = Ph, R ' = Cy；b, R = iPr, R ' = Cy；2, R = Ph, R ' = -CH (CH2OH)2；b, R = iPr, R ' = -CH (CH2OH)2；3a, R = Ph, R ' = -CH2CH (OH)CH2OH；3b, R = iPr, R ' = CH2CH(OH)CH2OH；4a (R = Ph, R ' = H；4b, R = iPr, R ' = H)。它们被分离为亮橙色或黄色固体，产率中等/良好。采用多核（1H,13C,31P） NMR、FT-IR、UV-Vis、高分辨质谱和循环伏安法对化合物进行了表征。化合物1b、2a、3a和4a、b也用单晶x射线衍射方法进行了表征。

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来源期刊

Phosphorus, Sulfur, and Silicon and the Related Elements 化学-无机化学与核化学

CiteScore

2.60

自引率

7.70%

发文量

103

审稿时长

2.1 months

期刊介绍： Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.