What explains caffeine's higher solubility in dichloromethane compared to water?

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Caffeine's higher solubility in dichloromethane compared to water is attributed to its molecular size and the nature of its dipole moment. Although caffeine has a larger dipole moment than water, its larger molecular structure leads to a lower overall polarity. This means that the charges within the caffeine molecule are more dispersed, reducing its interaction with polar solvents like water. Consequently, caffeine interacts more effectively with the nonpolar dichloromethane. The discussion highlights the complexity of solubility beyond simple polarity comparisons.
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Why caffeine is more soluble in dichloromethane than in water?
I thought caffeine is more polar than water and water is more polar than dichloromethane, so shouldn't caffeine is more soluble in water than in dichloromethane, since their dipole moment is closer?
 
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slft said:
I thought caffeine is more polar than water

Why do you think so?
 
cuz the dipole moment of caffeine is larger than water
 
This is not that simple. Caffeine molecule is much larger, so even small charge is separated over the large distance, which makes dipole moment large - but the molecule is not that polar.

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