Exploring the effect of substitution patterns on the symmetry of hydrogen-bonded supramolecular motifs in functionalized benzosiloxaboroles

Abstract

Crystal structures of a series of 26 functionalized 3-hydroxybenzo[c][1,2,3]siloxaboroles were compared taking into account electronic and steric effects of substituents at the aromatic ring on the hydrogen-bond (HB) motifs involving...

Exploiting thiol-functionalized benzosiloxaboroles for achieving diverse substitution patterns – synthesis, characterization and biological evaluation of promising antibacterial agents

“…S3 in the ESI † ) showing that the geometric parameters of benzosiloxaborole cores are similar as in structures reported previously. 45 …”

“…They were characterized by multinuclear NMR ( 1 H, 13 C, 11 B, 19 F, 31 P) spectroscopy and S3 in the ESI †) showing that the geometric parameters of benzosiloxaborole cores are similar as in structures reported previously. 45 Since acidity is an important parameter in medicinal chemistry, the pK a values of the benzosiloxaborole precursors 1e and 2e, as well as the selected promising compounds 6, 20 and 22-24 were measured (Table 2) by potentiometric titration with aq. 0.1 M NaOH in H 2 O/MeOH (1 : 1 v/v).…”

Ethynyl-substituted benzosiloxaboroles: the role of C(π)⋯B interactions in their crystal packing and use in Cu(i)-catalyzed 1,3-dipolar cycloaddition

“…The geometry of benzosiloxaborole core in 1c is essentially the same as in related compounds reported by us previously. 9 The supramolecular assembly of 1c shows centrosymmetric hydrogen-bonded (HB) dimers (O⋯O distance of 2.784(1) Å, motif D1, Fig. 1a) typical of boronic acid derivatives 22 including most of benzoxaboroles and many benzosiloxaboroles.…”

“…Recently, we have also studied crystal structures of functionalized benzosiloxaboroles showing that there is a strong effect of substitution pattern on their supramolecular assembly, mostly manifested by formation of various hydrogen-bonded motifs. 9 Those results revealed that benzosiloxaboroles are interesting also from the perspective of crystal engineering.…”