Binary and ternary co-crystals and molecular salts of 3,5-dinitrobenzoic acid: A many-faceted supramolecular reagent

Uncovering Cocrystal Formation and Competition Mechanism of Polyhydroxy Natural Products: Cases of Quercetin, Hesperidin, Resveratrol, and Curcumin

“…3,10 Currently, the prevailing view suggests that cocrystal formation depends on the development of weak intermolecular interactions between the active pharmaceutical ingredient (API) and the cocrystal forming factor (CCF). 11,12 These weak intermolecular interactions primarily encompass hydrogen bonding, π−π bonding, halogen bonding, and electrostatic interactions. 13,14 This study specifically focuses on the impact of hydrogen bonding on the formation of cocrystals between polyhydroxy natural products and CCFs, without considering other intermolecular weak interactions.…”

“…Cocrystallization is highly complex and can be influenced by various factors, such as weak intermolecular interactions and spatial site-barrier effects. , Currently, the prevailing view suggests that cocrystal formation depends on the development of weak intermolecular interactions between the active pharmaceutical ingredient (API) and the cocrystal forming factor (CCF). , These weak intermolecular interactions primarily encompass hydrogen bonding, π–π bonding, halogen bonding, and electrostatic interactions. , This study specifically focuses on the impact of hydrogen bonding on the formation of cocrystals between polyhydroxy natural products and CCFs, without considering other intermolecular weak interactions. , Polyhydroxy natural products possess numerous hydrogen bonding sites that can interact with CCFs to form cocrystals. By disregarding the influence of other forces within the crystals, these polyhydroxy natural products serve as an ideal model for investigating the effects of hydrogen bonding on cocrystal formation. , …”

Exploring the Crystal Structure Landscape of 3,5-Dinitrobenzoic Acid through Various Multicomponent Molecular Complexes

“…7−9 A total of 278 results of cocrystals and molecular salts have been reported. Studies involving dnba include high energy density related materials, 10,11 short, strong hydrogen bonding 12 and the crystal engineering of APIs. 13−15 Although the primary interactions will be due to the formation of a hydrogen bond between the carboxylic acid and a suitable hydrogen bond acceptor of the coformer, other types of weaker interactions exist and could contribute significantly.…”

“…Several multicomponent crystal structures, both binary and ternary, involving dnba have been published in the Cambridge Structural Database (CSD), including those which include various APIs. − A total of 278 results of cocrystals and molecular salts have been reported. Studies involving dnba include high energy density related materials, , short, strong hydrogen bonding and the crystal engineering of APIs. − Although the primary interactions will be due to the formation of a hydrogen bond between the carboxylic acid and a suitable hydrogen bond acceptor of the coformer, other types of weaker interactions exist and could contribute significantly. For example, π holes from the nitro groups can form directional intermolecular interactions between neighboring molecules .…”

Polymorphism and photoluminescence seen in (2-amino-5-chloropyridine)·(9-anthracenecarboxylic acid)·(trinitrobenzene): a further example of the salt-cocrystal continuum observed by virtue of isolating multiple crystal forms

“…9,10,11,12 To hold the starting components of these higher order cocrystals together, intermolecular interactions are employed. In most instances hydrogen bonding is coupled with other types of intermolecular interaction such as, halogen bonding 9,4 charge transfer, 10,13,14 and stacking interactions 1 . In this paper ternary adducts were synthesized using the method developed by Lemmerer and co-workers, whereby a combination of hydrogen bonding and charge transfer interactions are used to combine the three starting components.…”