Anion recognition by silanetriol in acetonitrile
Anion recognition by silanetriol in acetonitrile
复制标题
乙腈中硅烷三醇的阴离子识别
DOI：
10.1039/d2ob01596j
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Unno Masafumi
中科院分区：
文献类型：
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作者：
Kondo Shin-ichi;Okada Natsumi;Abe Shiori;Tanaka Ryoji;Yamamura Masaki;Unno Masafumi
用核磁共振氢谱滴定方法评价了2，4，6-三异丙基苯基硅三醇5在MeCN-d3中的阴离子识别能力。硅三醇5的阴离子识别能力强于结构相关的硅二醇和硅蒙脱醇，但不如1，3-二硅氧烷-1，3-二醇和1，3-二硅氧烷-1，1，3-四醇。从缔合常数的比较和密度泛函理论计算，5个硅醇的三个基团都与阴离子物种协同氢键。还考察了硅三醇5在CH2Cl2中对吲哚与β-硝基苯乙烯加成反应的催化性能。在该反应中，硅三醇5比相应的硅烷二醇起到了更有效的有机催化作用。
The anion recognition ability of 2,4,6-triisopropylphenylsilanetriol 5 has been evaluated by 1H NMR titrations in MeCN-d3. The anion recognition ability of silanetriol 5 was greater than those of the structurally related silanediols and silanemono-ol, although less effective than those of 1,3-disiloxane-1,3-diol and 1,3-disiloxane-1,1,3,3-tetraol. From the comparison of the association constants and DFT calculations, all three silanol groups of 5 cooperatively hydrogen bonded to anionic species. The catalytic ability of silanetriol 5 for the addition of indole to β-nitrostyrene in CH2Cl2 has also been evaluated. Silanetriol 5 acts as a more effective organocatalyst than the corresponding silanediol in this reaction.