Solid state bonding situation of benzyl silanes: Influence of an intramolecular ammonium group

Crystal structures, Hirshfeld atom refinements and Hirshfeld surface analyses of tris(4,5-dihydrofuran-2-yl)methylsilane and tris(4,5-dihydrofuran-2-yl)phenylsilane

“…The silicon atom in 1 has a slightly distorted tetrahedral environment, as shown by the deviation of the C-Si-C angles from the ideal value of 109.47 . This flexibility is often observed for Si-C single bonds (Otte et al, 2017;Glidewell & Sheldrick, 1971;Kü ckmann et al, 2005). The length of each of the C C double bonds of the DHF groups (C1 C2, C5 C6, C9 C10) also corresponds well with the literature (Allen et al, 1987).…”

Crystal structure and Hirshfeld surface analysis of 1-[(benzyldimethylsilyl)methyl]-1-ethylpiperidin-1-ium ethanesulfonate

“…The silicon center in 1 features a tetrahedral geometry, which is significantly distorted, as shown by the smallest angle of 98.35 (5) (C7-Si1-C10) and the largest angle of 114.32 (7) (C8-Si1-C10). This geometric distortion has been observed in many complex substituted silicon compounds and depends on the substituents (Otte et al, 2017). However, the distortion is large for compound 1 compared to most known silanes (Krupp et al, 2020).…”

“…Our group has focused on using lithium organyls as strong nucleophiles to perform these Si-C transformations on highly substituted silanes (Bauer & Strohmann, 2014). In particular, derivatives of -piperdinobenzylsilanes have been intensively studied by our group (Strohmann et al, 2004;Otte et al, 2017). When strong nucleophiles are used, deprotonation in the benzyl position competes with the selective Si-C bond cleavage of the benzyl group.…”

“…Consequently, the -character of the Si-C bond is more pronounced, leading to an elongation of the bond. Thus, a selective cleavage of the amino functionality due to the elongated Si-C bond is also conceivable (Bent, 1960(Bent, , 1961Otte et al, 2017).…”

Crystal structures of [(N,N-dimethylamino)methyl]ferrocene and (R p,R p)-bis{2-[(dimethylamino)methyl]ferrocenyl}dimethylsilane

“…112.17 (13) (C14-Si1-C16) as the largest. This flexibility is often observed for Si-C bonds (Otte et al, 2017). Compared to compound 1, the aminomethyl side chains are oriented in the direction of the silicon atom, but the NÁ Á ÁSi contact distances of 3.552 (3) for N2 and 3.584 (3) Å for N1 are too long to be regarded as coordinate bonds to Si from the N lone pairs.…”