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that protonates another substance. Upon protonating a substrate, the mass and the charge of the species each increase by one unit, making it an essential step in certain analytical procedures such as electrospray
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Protonation is usually reversible, and the structure and bonding of the conjugate base are normally unchanged on protonation. In some cases, however, protonation induces
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238:. Protonating or deprotonating a molecule or ion can change many other chemical properties, not just the charge and mass, for example
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217:. Some ions and molecules can undergo more than one protonation and are labeled polybasic, which is true of many biological
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Kramarz, K. W.; Norton, J. R. (1994). "Slow Proton
Transfer Reactions in Organometallic and Bioinorganic Chemistry".
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Protonations are often rapid, partly because of the high mobility of protons in many solvents. The
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can be especially slow when protonation induces significant structural changes.
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Addition of a proton to an atom, molecule, or ion, forming the conjugate acid
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Protonation is a fundamental chemical reaction and is a step in many
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62:. (The complementary process, when a proton is removed from a
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225:; they are the core of most acid–base reaction theories. A
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270:of protonation is related to the
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290:Reversibility and catalysis
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324:Acid dissociation constant
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70:.) Some examples include
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335:Molecular autoionization
354:Zumdahl, S. S. (1986).
121:in the formation of a
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306:can be converted to
172:in the formation of
418:Reaction mechanisms
252:oxidation potential
248:reduction potential
227:Brønsted–Lowry acid
223:acid–base reactions
215:catalytic processes
168:The protonation of
117:The protonation of
74:The protonation of
64:Brønsted–Lowry acid
18:Protonated molecule
413:Chemical reactions
331:(or dehydronation)
256:optical properties
231:chemical substance
312:serine hydrolases
236:mass spectrometry
178:hydrogen chloride
176:from ammonia and
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123:carbocation
36:hydronation
32:protonation
407:Categories
341:References
276:weak acids
240:solubility
356:Chemistry
119:isobutene
387:: 1–65.
318:See also
191:) + HCl(
52:molecule
304:alkenes
272:acidity
170:ammonia
362:
254:, and
195:) → NH
44:hydron
40:proton
308:trans
262:Rates
144:⇌ (CH
140:+ HBF
97:O ⇌ H
76:water
66:, is
54:, or
360:ISBN
268:rate
213:and
152:C +
136:C=CH
101:O +
48:atom
42:(or
34:(or
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300:cis
250:or
199:Cl(
128:(CH
103:HSO
93:+ H
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409::
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183:NH
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154:BF
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89:SO
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201:s
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193:g
189:g
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108:4
99:3
95:2
91:4
87:2
85:H
20:)
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