Compounds with Potential Amino Groups

Structure of Five-membered Rings with One Heteroatom 

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V. Compounds with Potential Substituted Amino Groups. , . 417... 

VI. Compounds with a Potential Hydroxy and a Potential Amino Group. 132... 

When dealing with the water solubility of ionized molecules, one also must consider the possibility of intramolecular ionic interactions. Compounds with ionizable functional groups that produce opposite charges have the potential to interact with each other rather than with water molecules. When this occurs, such compounds often become very insoluble in water. A classic example is the amino acid tyrosine (Fig. 2.11). Tyrosine contains three very polar functional groups, with two of these groups (the alkylamine and carboxylic acid) capable of being ionized, depending on the pH of the solution. The phenolic hydroxyl also is ionizable (pKg 9-10), but it... 

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