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In chemistry, a zwitterion ( ; from German ''zwitter'' (:ˈtsvɪtɐ) "hybrid" and formerly called a dipolar ion) is a neutral molecule with a positive and a negative electrical charge, though multiple positive and negative charges can be present. Zwitterions are distinct from dipoles, at different locations within that molecule. Zwitterions are sometimes also called inner salts.〔IUPAC Gold Book (''zwitterionic compounds/zwitterions'' )〕 Unlike simple amphoteric compounds that might only form ''either'' a cationic or anionic species depending on external conditions, a zwitterion simultaneously has both ionic states in the same molecule. ==Examples== Amino acids are the best-known examples of zwitterions. These compounds contain an ammonium and a carboxylate group, and can be viewed as arising via a kind of intramolecular acid–base reaction: The amine group deprotonates the carboxylic acid. :NH2RCHCO2H NH3+RCHCO2− The zwitterionic structure of glycine in the solid state has been confirmed by neutron diffraction measurements. At least in some cases, the zwitterionic form of amino acids also persists in the gas phase.〔 (text )〕 In addition to the amino acids, many other compounds that contain both acidic and basic centres tautomerize to the zwitterionic form. Examples, such as bicine and tricine, contain a basic secondary or tertiary amine fragment together with a carboxylic acid fragment. Neutron diffraction measurements show that solid sulfamic acid exists as a zwitterion. Many alkaloids, such as LSD and psilocybin, exist as zwitterions because they contain carboxylates and ammonium centres. Many zwitterions contain quaternary ammonium cations. Since it lacks N–H bonds, the ammonium center cannot participate in tautomerization. Zwitterions containing quaternary-ammonium centers are common in biology, a common example are the betaines, which serve as electrolytes in fish. The membrane-forming phospholipids are also commonly zwitterions. The polar head groups in these compounds are zwitterions, resulting from the presence of the anionic phosphate and cationic quaternary ammonium centres.〔Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.〕 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「zwitterion」の詳細全文を読む スポンサード リンク
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