Hydrogen bonded supramolecular structures of eight organic salts based on 2,6-diaminopyridine, and organic acids

Jin, Shouwen; Zhao, Ying; Liu, Bin; Jin, Xiunan; Zhang, Huan; Wen, Xianhong; Liu, Hui; Jin, Li; Wang, Daqi

doi:10.1016/j.molstruc.2015.06.054

Cited by 15 publications

(1 citation statement)

References 53 publications

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“…In addition, crystal structures containing 3-carboxylato-4-hydroxybenzenesulfonate dianion, C 7 H 4 O 6 S 2− (with a negative charge at both sulfonyl and carboxyl groups), and singly or doubly charged organic cations have been structurally characterized [1,[41][42][43][44]. Among them, the salts of C 7 H 4 O 6 S 2− with 2-aminopyridinium [45], 2,6-diaminopyridinium [46] 2-amino-4,6-dimethylpyrimidinium [47], and 6-(benzylamino)-3H-purin-7-ium ions [48] can also be distinguished.…”

Section: Introductionmentioning

confidence: 99%

Novel Salts of Heterocyclic Polyamines and 5-Sulfosalicylic Acid: Synthesis, Crystal Structure, and Hierarchical Supramolecular Interactions

Bojarska,

Łyczko,

Mieczkowski

2024

Crystals

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A series of novel salts of heterocyclic polyamines with 5-sulfosalicylic acid (C4H7N4+)(C7H5O6S−)∙2(H2O) (1), (C4H6ClN4+)(C7H5O6S−)∙H2O (2), (C5H8N3+)(C7H5O6S−)∙H2O (3), (C5H7N6+)(C7H5O6S−)∙H2O (4), (C6H14N22+)(C7H4O6S2−)∙H2O (5), and (C14H19N2+)(C7H5O6S−) (6) have been successfully synthesized. Their crystal structures have been determined by single-crystal X-ray diffraction. Overall, compounds adopt a layered structure with aminium cations and 5-sulfosalicylic anions linked via water molecules. The solid-state architectures of these compounds are dominated by O(N,H)-H⋯O and N-H⋯N hydrogen bonds and stabilized by weak interconnects. C-Cl⋯π and S-O⋯π interactions, apart from π⋯π and C-H(O)⋯π, were reported. Diverse approaches were used to study the effect of substituents in the polyamines in solid-state arrangement. A Hirshfeld surface analysis, with associated 3D Hirshfeld surface maps and 2D fingerprint plots, molecular electrostatic potential, and energy frameworks were used to comprehensively investigate the nature and hierarchy of non-covalent interactions and inspect supramolecular differences. The contact enrichment ratio calculations provided deeper insight into the propensity of interconnects to influence crystal packing. The evaluation of the effects of H-bonding synthons resulting from different substituents in the polyamines on self-assemblies is also presented. In the context of crystal engineering, a specific intramolecular synthon via O-H⋯O observed in nearly all crystals can be employed in the pseudo-cyclic replacement strategy in the design of new molecules.

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