2019
DOI: 10.1021/acs.cgd.8b01934
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Abstract: For a comprehensive analysis of host–guest binding propensity in their neutral form, three linear flexible bis-urea receptors (L 1 –L 3 ) with different terminal substituents have been synthesized. It has been established that, with the existence of electron-withdrawing or π-acidic phenyl substituents, they act as a possible system that can proficiently coordinate with anions of diverse dimensions constantly initiated by the size of the countercations. The 3,5-bis­(trifluoromethyl)­phenyl-derived isomer (L … Show more

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Cited by 6 publications
(4 citation statements)
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References 53 publications
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“…These obvious distinctions in the bond parameters occurred as a consequence of the differences in the ionic radii of the three halides. For the ionic cocrystals of the tetrabutylammonium halides with urea, , oximes suggest the requirement of hydrophobic space to accommodate the cation. , In the present case, the hydrophobic arms of the TBA are positioned in the hydrophobic concave part by the geometrically adjustable angular-shaped host in the assembly held by the C29–H···O interactions.…”
Section: Resultsmentioning
confidence: 70%
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“…These obvious distinctions in the bond parameters occurred as a consequence of the differences in the ionic radii of the three halides. For the ionic cocrystals of the tetrabutylammonium halides with urea, , oximes suggest the requirement of hydrophobic space to accommodate the cation. , In the present case, the hydrophobic arms of the TBA are positioned in the hydrophobic concave part by the geometrically adjustable angular-shaped host in the assembly held by the C29–H···O interactions.…”
Section: Resultsmentioning
confidence: 70%
“…The nitrification ability of urea derivatives has been enhanced by sulfa drugs . Some alkaline-earth-metal salts have been used to degrade urea derivatives, , and ionic cocrystals of urea have importance in the study of fertilizer actions. , Generally, charge-assisted hydrogen bonds have energy in the range between 12 and 25 kcal/mol, which provides stability to a halide-assisted assembly. Due to their electrostatic nature, the charge-assisted hydrogen bonds have higher strengths and such hydrogen bonds are possible in an self-assembly of a urea derivative. , Various urea and related compounds have been used as anion receptors of organic ammonium halides. Urea derivatives are commonly used to selectively detect fluoride ions over the other halide ions present in a solution. In these processes two issues get priority: one is the solvent, and the other is proton transfer from a chromogenic probe molecule.…”
Section: Introductionmentioning
confidence: 99%
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“…Diarylureas are frequently used in self-assembly, anion recognition, and cocrystallization as they can act as both H-bond donors through their double NH units and acceptors by the urea CO group. Etter has summarized complexing rules for diphenylureas taking 1,3-bis­( m -nitrophenyl)­urea as the model substrate in the early 1990s. , The major conclusion is that diarylureas with strong meta-substituted electron-withdrawing substituents have the property to bond with strong acceptor solvents or reagents such as dimethyl sulfoxide (DMSO) and triphenylphosphine oxide (TPPO) in a 1:1 stoichiometry. Later studies found that diarylureas could also recognize various anions including acid radicals, halides, and metal ions. Yamasaki et al recently reported the formation of a diphenylurea cocrystal between different diphenylureas . In addition, the introduction of heteroaromatic substitutions (e.g., pyridine) , and more H-bond donors or acceptors (e.g., NO 2 , pyrrole, I, F) in aromatic units would afford more diverse packing patterns. At the same time, Nanjia, Swift, and co-workers made great efforts to predict the cocrystallization and possible assembly styles from substitution environment, electronic effects, and with the help of computational energy calculation. , ,, …”
Section: Introductionmentioning
confidence: 99%