Virtual assessment achieved two binary cocrystals based on a liquid and a solid pyridine derivative with modulated thermal stabilities

Abstract

The melting point of a liquid and a solid pyridine derivative has been modified using the cocrystal formation approach by combination with two carboxylic acids. Their crystal packings have been analyzed and correlated with their thermal stability.

Structural Landscape of α-Acetamidocinnamic Acid Cocrystals with Bipyridine-Based Coformers: Influence of Crystal Packing on Their Thermal and Photophysical Properties

“…This methodology was successfully applied in our group in a previous work. 40 All the structures were energy-minimized using the COMPASS II force field in Materials Studio. 53,54 Then, geometry optimizations were done using the density functional theory (DFT) with B3LYP/6-31G(+) theory level with the Gaussian09 software version D.01.…”

“…40−42 The dihydrate structure connected the HACA molecules through masked synthons 43 of water clusters supported by acid•••amide interactions, 41,42 whereas the cocrystal contained 2-pyridone (Pdon), presenting Pdon•••acid and amide•••amide synthons. 40 However, previous studies performed in the group with coordination compounds suggested a tendency of the HACA molecules toward being ordered by amide•••amide patterns, leading to supramolecular chains or cycles depending on the synthetic conditions. 44−46 Therefore, in this work, we will evaluate the behavior of HACA when combined with bipyridine-type coformers benefiting from the well-known acid•••pyridine heterosynthon.…”

“…In addition, we recently applied virtual screening techniques to assess their feasible formation. 40 Following these works, in this contribution, we will focus on the study of the structural landscape of α-acetamidocinnamic acid (HACA), which contains an amide and a carboxylic acid moiety as functional groups. To date, only one dihydrate and one cocrystal have been reported.…”

“…In this context, the synthon competitivity between functional groups within a same molecule has been a major concern, − and even though a myriad of cocrystals with multifunctional molecules have been reported, − the control of their synthons remains poorly understood, and additional investigations are necessary aiming to find hierarchical combinations of supramolecular synthons referred to as supramolecular orthogonality − toward the design of advanced functional supramolecular materials. − Within this frame, our group has previously studied some cocrystals based on the acid···amide, and acid···pyridine , heterosynthons. In addition, we recently applied virtual screening techniques to assess their feasible formation . Following these works, in this contribution, we will focus on the study of the structural landscape of α-acetamidocinnamic acid (HACA), which contains an amide and a carboxylic acid moiety as functional groups.…”

“…Following these works, in this contribution, we will focus on the study of the structural landscape of α-acetamidocinnamic acid (HACA), which contains an amide and a carboxylic acid moiety as functional groups. To date, only one dihydrate and one cocrystal have been reported. − The dihydrate structure connected the HACA molecules through masked synthons of water clusters supported by acid···amide interactions, , whereas the cocrystal contained 2-pyridone (Pdon), presenting Pdon···acid and amide···amide synthons . However, previous studies performed in the group with coordination compounds suggested a tendency of the HACA molecules toward being ordered by amide···amide patterns, leading to supramolecular chains or cycles depending on the synthetic conditions. − …”