We present the preparation of tert-butyldiphenylsilanes differing in one functional group. The molecular structures of the phenyl (3), methoxy (4), and amino derivatives (5) were elucidated by single-crystal X-ray diffraction analysis and their crystal packing investigated by Hirshfeld surface analysis along with 2D fingerprint plots. In the all-C derivative 3, the high symmetry dependence of the crystal packing enables a multitude of directional C(methyl)−H⋅⋅⋅C(π) interactions between the tert-butyl and phenyl groups. The methoxy derivative 4 is characterized by considerably short H⋅⋅⋅H contacts possibly resulting from pre-orienting C(aryl)−H⋅⋅⋅O and C(aryl)−H⋅⋅⋅C(π) hydrogen bonds. In the amino derivative 5, the nitrogen atom is not involved in intermolecular interactions, instead dispersive H⋅⋅⋅H contacts might become more important for the crystal cohesion. These findings once again underline the pronounced lone electron pair density transfer from the nitrogen atom towards the silicon atom.

中文翻译：

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叔丁基二苯基硅烷 (TBDPS) 中的官能团变化：合成、反应性以及对分子结晶状态下分子间相互作用模式的影响

我们介绍了一种官能团不同的叔丁基二苯基硅烷的制备。通过单晶 X 射线衍射分析阐明了苯基 ( 3 )、甲氧基 ( 4 ) 和氨基衍生物 ( 5 )的分子结构，并通过 Hirshfeld 表面分析和二维指纹图研究了它们的晶体堆积。在全C衍生物3 中，晶体堆积的高度对称性依赖性使叔丁基和苯基之间的大量定向 C(甲基)−H⋅⋅⋅C(π) 相互作用成为可能。甲氧基衍生物4其特点是相当短的 H⋅⋅⋅H 接触可能是由于预先定向的 C(芳基)−H⋅⋅⋅O 和 C(芳基)−H⋅⋅⋅C(π) 氢键造成的。在氨基衍生物5 中，氮原子不参与分子间相互作用，相反，分散的 H⋅⋅⋅H 接触可能对晶体内聚力变得更加重要。这些发现再次强调了从氮原子到硅原子的显着孤电子对密度转移。