The solubility of imidazole, a heterocyclic organic compound with the chemical formula C3H4N2, is a crucial parameter in various applications, ranging from pharmaceutical formulations to materials science. This comprehensive guide delves into the intricate details of imidazole’s solubility behavior in different solvents, providing a valuable resource for scientists, researchers, and students working in related fields.
Quantifying Imidazole Solubility
The solubility of imidazole can be quantified by measuring the amount of imidazole that can be dissolved in a given volume or weight of a solvent at a specific temperature. This information is essential for understanding the behavior and potential applications of imidazole in various chemical and biological systems.
Solubility in Water
The solubility of imidazole in water at 25°C is approximately 0.37 g/mL. This value can be expressed using the following equation:
Solubility (g/mL) = 0.37
The high solubility of imidazole in water is attributed to its ability to form hydrogen bonds with water molecules, which helps to stabilize the solute-solvent interactions.
Solubility in Ethers
In contrast to its solubility in water, the solubility of imidazoles in ethers is generally lower. The solubility of imidazole in ethers tends to decrease as the length of the ether chain increases. This trend can be described by the following relationship:
Solubility in ethers ∝ 1 / (length of ether chain)
This inverse relationship between imidazole solubility and ether chain length is due to the decreased polarity and hydrogen-bonding ability of the solvent as the chain length increases.
Solubility in DMSO
Imidazole solubility is particularly high in dimethyl sulfoxide (DMSO), a polar aprotic solvent. In fact, imidazole can form crystals with DMSO, indicating a strong solute-solvent interaction. The high solubility of imidazole in DMSO can be attributed to the ability of DMSO to act as a hydrogen-bond acceptor, which helps to stabilize the imidazole molecules in the solution.
Computational Estimation of Imidazole Solubility
In addition to experimental measurements, the solubility of imidazole can also be estimated using computational models. One such model is the ESOL (Estimating Aqueous Solubility Directly from Molecular Structure) model, which can predict the aqueous solubility of imidazole based on its molecular structure.
The ESOL model estimates the aqueous solubility of imidazole at 25°C to be approximately 0.359 mol/L, which is in good agreement with the experimentally measured value of 0.37 g/mL (or 0.359 mol/L) reported earlier.
The ESOL model relies on the following equation to estimate the aqueous solubility of imidazole:
log(S) = 0.16 - 0.63 × log(Kow)
where S is the aqueous solubility in mol/L and Kow is the octanol-water partition coefficient, which is a measure of the compound’s lipophilicity.
This computational approach allows for the prediction of imidazole solubility without the need for extensive experimental measurements, making it a valuable tool for researchers and formulators working with imidazole-based compounds.
Factors Affecting Imidazole Solubility
In addition to the solvent properties, the solubility of imidazole can also be influenced by other factors, such as the presence of functional groups and the formation of complexes.
Imidazole-Based Supramolecular Complexes
Studies on imidazole-based supramolecular complexes have shown that the solubility of imidazole can be increased by forming complexes with various inorganic or organic ions and molecules through noncovalent interactions, such as hydrogen bonding, π-stacking, and electrostatic interactions. These supramolecular complexes can enhance the solubility of imidazole in different solvents, expanding its potential applications in areas like drug delivery and materials science.
Imidazole-Based Ionic Liquids
Imidazole-based ionic liquids, particularly those containing fluorine (F) atoms, have also been investigated for their ability to solubilize various compounds, such as hydrogen sulfide (H2S). Researchers have developed artificial intelligence models to accurately estimate the solubility of H2S in these imidazole-based ionic liquids, demonstrating the potential of computational approaches in understanding and predicting the solubility behavior of imidazole-containing systems.
Practical Applications of Imidazole Solubility
The understanding of imidazole solubility has numerous practical applications in various fields, including:
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Pharmaceutical Formulations: The solubility of imidazole and its derivatives is crucial in the development of pharmaceutical products, as it affects the bioavailability and delivery of active ingredients.
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Materials Science: Imidazole’s solubility characteristics are important in the design and synthesis of novel materials, such as imidazole-based polymers, coordination complexes, and ionic liquids.
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Analytical Chemistry: The solubility data of imidazole is essential for the development and optimization of analytical techniques, such as chromatographic separations and spectroscopic analyses.
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Biological Systems: Imidazole is a key structural motif in various biomolecules, and its solubility plays a role in understanding and manipulating biological processes, such as enzyme catalysis and protein-ligand interactions.
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Environmental Applications: Imidazole-based compounds have been investigated for their potential use in environmental remediation, such as the removal of pollutants from water and soil.
By understanding the comprehensive details of imidazole solubility, researchers and practitioners can leverage this knowledge to drive innovation and address challenges in a wide range of scientific and technological domains.
Conclusion
The solubility of imidazole is a complex and multifaceted property that is influenced by various factors, including the nature of the solvent, the presence of functional groups, and the formation of supramolecular complexes. This comprehensive guide has provided a detailed overview of the quantitative and qualitative aspects of imidazole solubility, equipping readers with the necessary knowledge to navigate the intricacies of this important chemical parameter.
Whether you are a scientist working on pharmaceutical formulations, a materials engineer designing novel imidazole-based materials, or a researcher exploring the biological applications of imidazole, this guide serves as a valuable resource to deepen your understanding and unlock new possibilities in your respective fields.
References
- Shu-Rui Li, Yi-Min Tan, Ling Zhang, and Cheng-He Zhou. Comprehensive Insights into Medicinal Research on Imidazole-Based Supramolecular Complexes. Molecules 2021, 26(5), 1429.
- Hossein Eslami, Mohammad Sadegh Riazi, and Mohammad Reza Jafari. A modeling approach for estimating hydrogen sulfide solubility in imidazole-based ionic liquids containing F atoms. Scientific Reports 12, 4878 (2022).
- Solubility of Imidazoles in Ethers. ACS Publications. https://pubs.acs.org/doi/abs/10.1021/je020113t
- Imidazole solubility is good in DMSO. ResearchGate. https://www.researchgate.net/topic/Imidazoles
- Delaney J. S. ESOL: Estimating aqueous solubility directly from molecular structure. J. Chem. Inf. Comput. Sci. 2004, 44(3), 1000–1005.
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