# Why are amines more soluble than ethers in water?

For example, diethyl ether ($\ce{C2H5OC2H5}$) has a limited solubility of $6.05\rm~\frac{g}{100~mL}$ water at $25\rm~^\circ C$. However, diethylamine ($\ce{(C2H5)2NH}$) is a lot more soluble in water. Why are ethers less soluble than amines? Both can form 2 hydrogen bonds with water (ethers accept two H-bonds, and amines donate an H-bond and accept an H-bond). Oxygen is more electronegative than nitrogen, so shouldn't ethers be more soluble?

• Consider chemical interactions between water and each of these, not just physical interactions. Mar 19 '16 at 19:26