Diversified self-association through O-H center dot center dot center dot O hydrogen bonds in crystals of formylphenylboronic acid isomers

作者：Madura Izabela D^*; Adamczyk Wozniak Agnieszka; Sporzynski Andrzej

来源：Journal of Molecular Structure, 2015, 1083: 204-211.

DOI：10.1016/j.molstruc.2014.11.072

• Formylphenylboronic acid
• Crystal structure
• Hydrogen bonding
• Large synthons
• Hirshfeld surface analysis

Numerous applications of formylphenylboronic acid isomers in organic synthesis as well as co-crystals' design and surface immobilization prompted us to study the effect of substituent position on their molecular and crystal structures. It has been found that changes in molecular geometry of ortho, meta and para derivatives are negligible, except differences in a twist of the -B(OH)(2) fragment towards phenyl ring. The lability of boronic moiety was attributed to diversified O-H center dot center dot center dot O hydrogen bonding patterns formed by its hydroxyl groups. The analysis of molecular packing was based on elucidation of hierarchical self-associated structural units. The identification of important, directional intermolecular interactions in crystal structures was supported by the Hirshfeld surface analysis. Subsequent supramolecular levels have been distinguished taking into account estimated energy of O-H center dot center dot center dot O bonds, dimensionality of large synthons and their symmetry. The resulting basic O-H center dot center dot center dot O motives are in form of dimers, undulated layers or chains. They are further joined by pi center dot center dot center dot pi interactions constituting the large synthons such as stacking columns or double layers.

• 出版日期2015-3-5