deprotonate

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deprotonation

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/05/22 16:49:47」(JST)

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Deprotonation is the removal of a proton (H⁺) from a molecule, forming the conjugate base.

The relative ability of a molecule to give up a proton is measured by its pK_a value. A low pK_a value indicates that the compound is acidic and will easily give up its proton to a base. The pK_a of a compound is determined by many things, but the most significant is the stability of the conjugate base, which is determined mainly by the ability (or inability) of the conjugated base to stabilize the negative charge. The negative charge is stabilized when it is distributed on a large surface or a long chain. One of the mechanisms that distribute the negative charge on a longer chain or a ring is resonance. The solvent can also assist in the stabilization of the negative charge on a conjugated base.

Bases used to deprotonate depend on the pK_a of the compound. When the compound is not particularly acidic, and, as such, the molecule does not give up its proton easily, a base stronger than the commonly known hydroxides is required. Hydrides are one of the many types of powerful deprotonating agents. Common hydrides used are sodium hydride and potassium hydride. The hydride forms hydrogen gas with the proton from the other molecule. However, the production of hydrogen also means that deprotonation using agents that release hydrogen is dangerous and should be done in an inert atmosphere (e.g., nitrogen), as the hydrogen can ignite with the oxygen in the air.

See also

• Protonation
• Hydronium
• Acid dissociation constant

English Journal

• Complexes of a naphthalimide photoacid with organic bases, and their excited-state dynamics in polar aprotic organic solvents.

• Kumpulainen T1, Bakker BH, Brouwer AM.
• Physical chemistry chemical physics : PCCP.Phys Chem Chem Phys.2015 Aug 28;17(32):20715-24. doi: 10.1039/c5cp02556g. Epub 2015 Jul 24.
• Complex formation and intermolecular excited-state proton transfer (ESPT) between a dihydroxy-1,8-naphthalimide photoacid and organic bases are investigated in polar aprotic solvents. First, quantum chemical calculations are used to explore the acid-base and spectroscopic properties and to identify
• PMID 26204802

• Steric Effects on the Structures, Reactivity, and Coordination Chemistry of Tris(2-pyridyl)aluminates.

• García-Rodríguez R1, Wright DS2.
• Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2015 Aug 25. doi: 10.1002/chem.201502156. [Epub ahead of print]
• Introducing substituents in the 6-position of the 2-pyridyl rings of tris(pyridyl)aluminate anions, of the type [EtAl(2-py')3 ]- (py'=a substituted 2-pyridyl group), has a large impact on their metal coordination characteristics. This is seen most remarkably in the desolvation of the THF solvate [Et
• PMID 26308951

• Constant-pH Hybrid Nonequilibrium Molecular Dynamics-Monte Carlo Simulation Method.

• Chen Y1, Roux B1.
• Journal of chemical theory and computation.J Chem Theory Comput.2015 Aug 11;11(8):3919-3931. Epub 2015 Jun 18.
• A computational method is developed to carry out explicit solvent simulations of complex molecular systems under conditions of constant pH. In constant-pH simulations, preidentified ionizable sites are allowed to spontaneously protonate and deprotonate as a function of time in response to the enviro
• PMID 26300709

Japanese Journal

• Mechanism of the nucleotidyl-transfer reaction in DNA polymerase revealed by time-resolved protein crystallography

• BIOPHYSICS 9(0), 31-36, 2013
• NAID 130003366027

• Solution Equilibrium and EPR Study of the Dinuclear Copper(II) Complexes of Aminopolycarboxylic Acids with an Alcohol OH Group in the Alkyl Chain Linkage.

• Bulletin of the Chemical Society of Japan 65(11), 2910-2921, 1992
• NAID 130004147446

• Observation on the fragmentation of some tosylhydrazones using electrochemically generated superoxide ion.

• Bulletin of the Chemical Society of Japan 63(4), 1233-1236, 1990
• NAID 130001979789

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deprotonation、deprotonate

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脱プロトン化

「deprotonation」

　　[★]

• 脱プロトン、脱プロトン化

関

deprotonate

「脱プロトン化」

　　[★]

英

deprotonation、deprotonate

関

脱プロトン