Effect of hydrogen bonds and π⋯π interactions on the crystallization of phenyl-perfluorophenyl amides: understanding the self-organization of a cocrystal

Abstract

A series of N-arylbenzamides containing amide group and phenyl−perfluorinated rings were used as the smallest molecules to investigate the direct influence of hydrogen bond and aromatic donor-acceptor complementarity in the...

Mesoionic compounds: the role of intermolecular interactions in their crystalline design

“…One of the important challenges in crystal engineering is designing proposals for the crystallization mechanisms of organic compounds. As previously reported by our research group 20,[22][23][24][25][26][27][28][29] as well as in various discussions on the topic, 61 an agglomerate or nucleus of molecules that have been detected in solution is maintained through the additional stages of aggregation and crystal growth and therefore survive until the end of the crystallization process. Thus, the crystallization process is understood from the formation of nuclei of molecules still in solution surrounding by solvents molecules, in which the most stable and energetically cooperative blocks persist as the solvent evaporation process progresses, forming more complex nuclei until the formation of the final crystalline lattice.…”

“…Thus, the crystallization process is understood from the formation of nuclei of molecules still in solution surrounding by solvents molecules, in which the most stable and energetically cooperative blocks persist as the solvent evaporation process progresses, forming more complex nuclei until the formation of the final crystalline lattice. 20,22–29…”

“…This method enables one to identify the plausible crystallization nuclei that were the first to be formed based on the energetic differences of each dimer, and a crystallization mechanism can then be proposed. 20,22–29…”

“…This method enables one to identify the plausible crystallization nuclei that were the first to be formed based on the energetic differences of each dimer, and a crystallization mechanism can then be proposed. 20,[22][23][24][25][26][27][28][29] Thus, our research group has used supramolecular cluster demarcation with other tools to answer important questions in crystal engineering, which is fundamental knowledge in solid-state chemistry. Our studies have revealed that uncharged organic molecules present only stabilizing intermolecular interactions between all molecules of the supramolecular cluster.…”

“…Our studies have revealed that uncharged organic molecules present only stabilizing intermolecular interactions between all molecules of the supramolecular cluster. [19][20][21][22][23][24][25][26][27][28] We have recently applied this method to the study of crystals of di-, tri-, and tetraalkyl ammonium halides, making it possible to verify, in addition to stabilized intermolecular interactions, the existence of destabilizing intermolecular interactions. 29 The energy diagrams of the supramolecular clusters of N-phenyl-2,2,2tribromoacetamide 28 and dimethylammoniumbromide 29 are illustrated in Fig.…”