Multifunctional Organosulfonate Anions Self-Assembled with Organic Cations by Charge-Assisted Hydrogen Bonds and the Cooperation of Water

Abstract

The present study focuses on the assembly of organo-cations with organo-anions in water. The anions, characterized by symmetric moieties (carbon-, adamantane-or calixarenebased) functionalized with directional hydrogen bond (HB) acceptor functions (tetra-sulfonate moieties), are combined with planar guanidinium or terephtalimidamide cations as hydrogen bond donors, the purpose being to integrate water molecules into the lattice. The imbalance between the charge on the two components, and the considerable number of HB donor and acceptor sites, promotes the insertion of water into the structures. In the reported structures, a part of the water molecules serves as a structural linker between the anions and cations while the remaining molecules cluster into channels and cavities in a loose association with the supramolecular matrix framework.

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

“…Mugheirbi and Tajber analyzed the FIM hotspots around the itraconazole molecule to understand the molecular environment in the mesophase [260]. The itraconazole lacks any donors of strong H-donors but has a number of competing acceptors of H- This tool has been applied mainly for the analysis of strong hydrogen bonds [54,170,190,194,[248][249][250][251] in accord with the first test functional groups suggested within this tool, and the first paper published to describe it. Mutual disposition of hot spots can be used to find functional groups of the same molecule [245], co-formers [243,249,250], active sites in a binding pocket of a macromolecule [252], or surface inhibitors [170], which match a given pattern of interaction preferences.…”

“…Instead, it more readily interacts with unsatisfied acceptors of H-bonding, especially R 2 PO 2 -, Cl -, C-NH 3 + groups, acts as a bridge between unsatisfied donors and acceptors, and occupies the free volume, especially for chiral molecules [290]. The strong imbalance between the number of donors and acceptor groups between tetrasulfonate-functionalized rigid anions and planar polyamino-containing cations indeed afforded their crystallization as hydrates, where water molecules act both as bridges between cations and anions, and clusters incorporated within cavities and channels of H-bonded networks [251]. Nevertheless, typically it is still hardly possible to predict if a compound will form a hydrate or not.…”

“…bonded networks [251]. Nevertheless, typically it is still hardly possible to predict if a compound will form a hydrate or not.…”

“…Various mobility of the water clusters incorporated within the pores and H-bonding waters that structure these pores was demonstrated in Refs. [251,307]. Liu et al demonstrated that anhydrous uric acid and its' dihydrate exhibited various mechanical properties of their single crystals despite the similarity of layered motifs formed by the acid [276].…”

Peculiarities of supramolecular organization of cyclic ketones with vinylacetylene fragments

“…Although C-HÁ Á ÁO hydrogen bonds are weak, we demonstrated previously (Voronova et al, 2016) that the Full Interaction Maps (FIMs) tool (Wood et al, 2013) implemented within the Mercury package (Macrae et al, 2008) can be applied to estimate likely C-HÁ Á ÁO hydrogen-bonded motifs for chalcones, polyenones and pentenynones. This result is of importance because previously the tool had been applied mainly for the analysis of strong hydrogen bonds (Mugheirbi & Tajber, 2015;George et al, 2015;Vologzhanina et al, 2016;Sandhu et al, 2018;Wojnarska et al, 2018;Xing et al, 2018). Thus, in this article, we have also applied FIMs to investigate C-HÁ Á ÁO and C-HÁ Á ÁBr hydrogen bonding in order to understand the effectiveness of a priori prediction of intermolecular interactions in this family.…”