Hydrogen Bond Hierarchy: Persistent Phenol···Chloride Hydrogen Bonds in the Presence of Carboxylic Acid Moieties

Abstract

Crystal engineering strategies have been delineated during the last decade for the design of multiple-component molecular crystals (molecular cocrystals, MCCs). However, the same depth of understanding has not yet been established for cocrystals that are comprised of at least one ionic compound (ionic cocrystals, ICCs). We address this long known but understudied class of cocrystals through the use of organic cation chloride salts as cocrystal formers with

Atom interaction propensities of oxygenated chemical functions in crystal packings

“…In both alcohol-monohydrate and phenol-monohydrate crystals, the presence of water molecules facilitates the formation of hetero-contacts between alcohol/phenol and water moieties. The hydrogen-bond hierarchy in compounds containing both a carboxylic acid/phenol moiety and a chloride anion was studied by the Zaworotko group (Duggirala et al, 2015). The presence of competing hydrogenbonding groups such as the water molecule was shown to disrupt the hydrogen-bond network existing in its absence (COOHÁ Á ÁCOOH, COOHÁ Á ÁCl À , PhOHÁ Á ÁPhOH, PhOHÁ Á ÁCl À ).…”

A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study

“…To date, various supramolecular frameworks comprising homo-synthons, occurring between the same functional groups, as well as heterosynthons, occurring between disparate functional groups, have been described. Molecules with carboxylic acid functionality remain at the forefront of co-crystal technology based on hydrogen-bonded synthons (Duggirala et al, 2015). Despite expectations to the contrary, the carboxylic acidÁ Á Ácarboxylic acid homo-synthon, i.e.…”

Interplay between Polymorphism and Isostructurality in the 2-Fur- and 2-Thenaldehyde Semi- and Thiosemicarbazones

“…Through the years, crystal engineering principles have been developed on the basis of crystallographic data. The hydrogen bond rules [8,9], exchange rule [10,11], synthon hierarchy for some functional group [12][13][14][15][16], and molecular tectonics [17][18][19] are the most important principles among all of the studied ones. They are very helpful in predicting the results of crystal formation, but are still insufficient.…”