[4‐(Ph3B)‐2,6‐Mes2Py]−: A Sterically Demanding Anionic Pyridine,Chemistry - A European Journal

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[4‐(Ph3B)‐2,6‐Mes2Py]−: A Sterically Demanding Anionic Pyridine
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-10-17 , DOI: 10.1002/chem.201803626
Nadja M. C. Schmidlin ₁ , Märt Lõkov ₂ , Ivo Leito ₂ , Tobias Böttcher ₁

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The introduction of a triphenylborate group at the 4‐position of 2,6‐dimesitylpyridine afforded a sterically demanding anionic pyridine. The charge introduced through the borate group drastically increases its basicity and measurement of its pK_a value (18.46) revealed a significantly higher value than that of 4‐dimethylaminopyridine (17.95). THF ring‐opening was observed upon treating its lithium salt with TMSCl, which demonstrates its high nucleophilicity. The mesityl groups at the 2,6‐positions are oriented orthogonal to the pyridine ring and do not block the nitrogen atom of the pyridine. The reaction of the protonated pyridine with Li[BH₄] yielded the corresponding Lewis acid/base adduct, which shows that the title compound can be used as a monodentate ligand in coordination chemistry. The crystal structures of all the compounds presented in this work are reported.

中文翻译：

[4-（Ph3B）-2,6-Mes2Py]-：立体上需要的阴离子吡啶

在2,6-二甲磺基吡啶的4位上引入硼酸三苯酯基团可提供空间上要求很高的阴离子吡啶。通过硼酸盐基团引入的电荷极大地提高了其碱性，其p K _a值（18.46）的测量值显着高于4-二甲基氨基吡啶（17.95）。用TMSCl处理锂盐后，可观察到THF开环，这表明它具有很高的亲核性。在2,6-位的均三基团的取向与吡啶环正交，并且不阻断吡啶的氮原子。质子化吡啶与Li [BH ₄产生相应的路易斯酸/碱加合物，表明标题化合物可在配位化学中用作单齿配体。报告了这项工作中出现的所有化合物的晶体结构。

更新日期：2018-10-17

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