Hydrogen bonded binary molecular adducts derived from exobidentate N-donor ligand with dicarboxylic acids: Acid⋯imidazole hydrogen-bonding interactions in neutral and ionic heterosynthons

Kathalikkattil, Amal Cherian; Damodaran, Subin; Bisht, Kamal Kumar; Suresh, Eringathodi

doi:10.1016/j.molstruc.2010.11.022

Cited by 22 publications

(5 citation statements)

References 43 publications

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“…It has been shown that components with DpK a < À1 form mostly cocrystals, while systems with DpK a > 4 tend to form exclusively salts. This ''rule'' has been also adjusted to various drug/coformer pairs (Kathalikkattil et al, 2011;da Silva et al, 2013;Sanphui et al, 2013;Elacqua et al, 2013;Thomas et al, 2014), despite the fact that DpK a range between 0 and 3 remains hardly predictable. For ciprofloxacin (pK a = 8.74 for the piperazine fragment (Ross and Riley, 1990)) and coformers of interest, however, the DpK a values are considerably greater than 3 units, which strongly suggests proton transfer and salt formation to occur.…”

Section: Resultsmentioning

confidence: 99%

Pharmaceutical salts of ciprofloxacin with dicarboxylic acids

Surov

Manin

Voronin

et al. 2015

European Journal of Pharmaceutical Sciences

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Section: Resultsmentioning

confidence: 99%

Pharmaceutical salts of ciprofloxacin with dicarboxylic acids

Surov

Manin

Voronin

et al. 2015

European Journal of Pharmaceutical Sciences

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“…Similarly, fumaric acid (A2) and malonic acid (A3) also showed the formation of monocarboxylate salt (one carboxylic acid CO asymmetric (1667–1669 cm –1 ) and one carboxylate CO stretching (1616 cm –1 )) with B1, B2, and B3. Understandably, very low p K 1 values of fumaric acid, maleic acid, and malonic acid, as compared with 2-aminothiazole, lead to the formation of monocarboxylate salts of these acids (difference between p K of acid and amine (Δp K ) =3 or more leads to the formation of salts), , whereas other aliphatic dicarboxylic acids resulted in the formation of cocrystals except decanedioic acid (A6) formed monocarboxylate ( B3A6 ) as well as dicarboxylate salts ( B3A6a ). The formations of cocrystals/salts were confirmed by single crystal X-ray studies in most of the cases.…”

Section: Resultsmentioning

confidence: 99%

Combinatorial Library Approach to Realize 2-Aminothiazole-Based Two-Component Hydrogelator: A Structure–Property Correlation

Yadav

Dutta

Ballabh

2014

Crystal Growth & Design

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Crystal engineering and supramolecular synthons approach are applied to synthesize a series of 2aminothiazole (and its methyl derivatives) salts/cocrystals with various dicarboxylic acids. On the basis of combinatorial library approach, 24 new salts/cocrystals of 2-aminothiazole and its methyl derivatives with various dicarboxylic acid (aliphatic unsaturated and saturated backbone) were synthesized and characterized. All the synthesized salts were subjected to gelation test in various solvents (polar and nonpolar). Interestingly, one of the salts/cocrystals, i.e., B3A6 (5methyl-2-aminothiazolium hydrogen decandioate) was found to be capable of immobilizing water at slightly higher minimum gelator concentration (MGC). A structure−property correlation between various cocrystals/salts based on single crystal X-structure of 11 compounds was undertaken. The gelation property of 2-aminothiazole-based gelling agent was found to be governed by the position of a methyl group on the thiazole ring, a length of the aliphatic carbon chain of dicarboxylic acid, and formation of hydrogen bonded network (HBN) leading to void in the single crystal structure. The comparison of single crystal X-ray structures of nongelators and a gelator were undertaken to understand the probable mechanism of hydrogelation in the series of 2-aminothiazole-based salts/cocrystals.

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“…The dicarboxylate anions can exhibit multiple coordination motifs such as uni-bidentate, bis-monodentate, bis-bidentate, tridentate, and tetradentate etc., thereby interconnecting metal centers to form polynuclear complexes [27,28]. Saturated dicarboxylic acids also serve as suitable H-bonding acceptors [29,30], resulting in the development of bridging metal-organic compounds with various desired self-assembled architectures [31,32]. As a consequence, adipic acid has evolved as a potential bridging ligand to form interesting coordination polymers with potential applications [33][34][35].…”

Section: Introductionmentioning

confidence: 99%

On the Importance of H-Bonding Interactions in the Enclathration of Boric Acids in Na(I) Polymers: Experimental and Theoretical Studies

et al. 2023

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Two Na(I) coordination polymers, namely, {Na(BA)2(μ-H2O)2}n{adp}n (1) and {[Na2(μ-BA)(μ-fum)(μ-H2O)4](BA)}n (2) (where, BA = boric acid, adp = adipic acid, fum = fumarate),were prepared and characterized using elemental analysis, TGA, FT-IR, and single-crystal X-ray diffraction techniques. Various unconventional supramolecular interactions, i.e., CH∙∙∙HC and parallel CO∙∙∙CO interactions, stabilize the layered assembly of compound 1. Interesting dual enclathration of BA molecules within the supramolecular host cavities formed by O-H∙∙∙O and C-H∙∙∙C interactions stabilizes the crystal structure of compound 2. The H-bonding interactions in 1 and 2 were further studied theoretically using the quantum theory of atoms in molecules (QTAIM) and the noncovalent interaction plot (NCI Plot) computational tools. The energy of the H-bonds was estimated using the potential energy density at the bond critical points. Theoretical calculations confirmed the presence of O-H∙∙∙O H-bonding interactions in both compounds, forming structure-guiding R22(8) synthons relevant for the stability of the compounds.

show abstract

Hydrogen bonded binary molecular adducts derived from exobidentate N-donor ligand with dicarboxylic acids: Acid⋯imidazole hydrogen-bonding interactions in neutral and ionic heterosynthons

Cited by 22 publications

References 43 publications

Pharmaceutical salts of ciprofloxacin with dicarboxylic acids

Pharmaceutical salts of ciprofloxacin with dicarboxylic acids

Combinatorial Library Approach to Realize 2-Aminothiazole-Based Two-Component Hydrogelator: A Structure–Property Correlation

On the Importance of H-Bonding Interactions in the Enclathration of Boric Acids in Na(I) Polymers: Experimental and Theoretical Studies

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