Which intermolecular interactions contribute most to the water solubility of drugs?

Question

BlackTom AI · Accepted Answer

Water is a highly polar solvent that both donates and accepts hydrogen bonds, so solubility in water is dominated by interactions that strongly stabilize solute molecules or ions in an aqueous environment: hydrogen bonding and ion–dipole interactions.

1) Relevant knowledge points and concepts
- Water polarity and H-bonding: each water molecule can form hydrogen bonds (H-bonds) with suitable donors/acceptors on solutes (OH, NH, carbonyls).  
- Ion–dipole interactions: charged (ionized) drug groups (e.g., protonated amines, deprotonated carboxylates, salts) interact strongly with the water dipole, producing strong solvation.  
- Relative strengths: dispersion (London) forces are weak and non-specific; dipole–dipole interactions are moderate; hydrogen bonds and ion–dipole interactions are substantially stronger and more effective at promoting aqueous solubility.

2) Step-by-step reasoning
- Step 1: Determine what water can provide: strong dipole and H-bond capability.  
- Step 2: For neutral polar drugs, H-bond donors/acceptors form favorable H-bonds with water, increasing solvation energy and solubility.  
- Step 3: For ionizable drugs, ionization produces charges that are stabilized by ion–dipole interactions with water; this stabilization strongly favors dissolution.  
- Step 4: Compare other interactions: dispersion forces and dipole–dipole interactions are weaker and do not overcome hydrophobic effects as effectively.

3) Calculations/intermediate steps
- No numerical calculation is required here; the intermediate logical comparisons are: dispersion << dipole–dipole < hydrogen bonding ≲ ion–dipole (ion–dipole often strongest for charged species).

4) Why the correct answer is correct
- Hydrogen bonding directly complements water’s H-bond network for neutral polar groups; ion–dipole interactions strongly solvate charged groups. Together these two interactions most effectively lower free energy of transfer into water, giving the greatest increase in solubility.

5) Why other options are incorrect
- a) “Ionic interactions and dispersion forces”: ionic interactions between solute ions (ion–ion) tend to favor precipitation (not solvation); dispersion forces are weak.  
- b) “Dispersion forces and hydrogen bonding”: dispersion is weak and cannot account for high solubility of ionized drugs.  
- c) “Dipole–dipole and dispersion forces”: both are weaker than H-bonding and ion–dipole and insufficient to explain good aqueous solubility, especially for charged drugs.

6) Conclusion
Hydrogen bonding and ion–dipole interactions (choice d) are the primary contributors to water solubility of drugs. This matches the provided correct answer.

Which intermolecular interactions contribute most to the water solubility of drugs?单项选择题

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What type of bonding interactions are possible at positions (i) O-H and (iii) N+, respectively, of the following drug?

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Which intermolecular interactions contribute most to the water solubility of drugs?单项选择题

类似问题

Which intermolecular interactions contribute most to the water solubility of organic compounds? A. ionic interactions and dispersion forces B. hydrogen bonding and ion-dipole interactions C. dispersion forces and hydrogen bonding D. dipole-dipole interactions and dispersion forces

Which intermolecular interactions contribute most to the water solubility of organic compounds? A. ionic interactions and dispersion forces B. hydrogen bonding and ion-dipole interactions C. dispersion forces and hydrogen bonding D. dipole-dipole interactions and dispersion forces

Question at position 3 Which of the following intermolecular forces is/are demonstrated by pure CH3F? Choose the single best answer. 1. hydrogen bonding 2. ionic forces 3. dispersion forces 4. dipole-dipole forces 3 only1 only2 and 4 only3 and 4 only4 only2 only1 and 3 only1 and 2 only

Match the following 1: Halogen bonding is ____ 2: Van der Waals interactions are caused by the ____ 3: Dipolar interactions result ____ 4: The cation-π interaction is a ____

Which of the following is incorrect about intermolecular forces?[Fill in the blank]

What type of bonding interactions are possible at positions (i) O-H and (iii) N+, respectively, of the following drug?

What type of bonding interactions are possible at positions (i) O-H and (iii) N+, respectively, of the following drug?

更多留学生实用工具

希望你的学习变得更简单

Match the following 1: Halogen bonding is 2: Van der Waals interactions are caused by the 3: Dipolar interactions result 4: The cation-π interaction is a