48:
328:
Davlieva, Milya G.; Lindeman, Sergey V.; Neretin, Ivan S.; Kochi, Jay K. (2004). "Structural effects of carbon monoxide coordination to carbon centers. σ and π Bindings in aliphatic acyl versus aromatic aroyl cations".
410:
Le
Carpentier, J. M.; Weiss, R. (1972). "Etude de complexes acide de Lewis–halogénure d'acide. I. Structure cristalline des hexachloroantimonate, tétrachloroaluminate et tétrachlorogallate de méthyl oxocarbonium".
356:
Esselman, Brian J.; Hill, Nicholas J. (2015). "Proper
Resonance Depiction of Acylium Cation: A High-Level and Student Computational Investigation".
308:
63:(which also has a C-O triple bond). They are typically prepared by removal of chloride from acyl chlorides using strong Lewis acids such as
135:). These values are 2300 and 2200 cm, respectively for the aryl and alkyl acylium ions. For comparison, the same vibration for
461:
55:
In acylium ions, the C-C-O linkage is linear. The oxygen and the central carbon can be described as sp hybridized. A
383:
Boer, F. Peter (1968). "Crystal structure of a
Friedel-Crafts intermediate. Methyloxocarbonium hexafluoroantimonate".
151:
as evidenced by their ability to attack arenes. Acylium ions are intermediates in several reactions, such as the
83:
213:
Such depictions may be simplistic because of ion-pairing between the acetyl cation (an acylium cation) and the
152:
64:
298:
456:
164:
71:
466:
420:
214:
121:
117:
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derivatives. Because acylium cation is highly electrophilic, its salts can only be isolated with
304:
221:
28:
451:
428:
392:
365:
338:
160:
136:
60:
424:
445:
148:
413:
59:
exists between C and O. Acylium ions can be viewed as C-alkylated derivatives of
294:
56:
36:
35:
are cations with the formula RCO, where R = alkyl or aryl. They are a kind of
432:
75:
396:
224:
is unusual because it exists in equilibrium with the tert-butyl cation:
79:
17:
369:
342:
47:
156:
46:
300:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
254:
is the hydrolysis of acylium ions to carboxylic acids:
131:
bond is indicated by the frequency of its vibration (ν
70:Several acylium salts have been characterized by
303:(6th ed.), New York: Wiley-Interscience,
8:
385:Journal of the American Chemical Society
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51:Structural details of the acetyl cation.
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1:
358:Journal of Chemical Education
220:The acylium ion derived from
43:Structure, bonding, synthesis
483:
124:are other early examples.
84:weakly coordinating anions
433:10.1107/S0567740872004406
331:New Journal of Chemistry
153:Friedel-Crafts acylation
147:Acylium ions are potent
462:Reactive intermediates
65:antimony pentachloride
52:
165:aluminium trichloride
72:X-ray crystallography
50:
215:tetrachloroaluminate
127:The strength of the
122:hexachloroantimonate
118:hexafluoroantimonate
425:1972AcCrB..28.1421L
397:10.1021/ja01026a025
293:Smith, Michael B.;
163:in the presence of
252:Koch carbonylation
205:R + HCl + AlCl
53:
391:(24): 6706–6710.
370:10.1021/ed5002152
310:978-0-471-72091-1
222:pivaloyl chloride
29:organic chemistry
16:(Redirected from
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437:
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419:(5): 1421–1429.
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250:Central to the
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161:acetyl chloride
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137:carbon monoxide
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61:carbon monoxide
45:
23:
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5:
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364:(4): 660–663.
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237:CCO ⇌ (CH
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149:electrophiles
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95:COCl + GaCl
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457:Carbocations
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337:(12): 1568.
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295:March, Jerry
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219:
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146:
139:is 2143 cm.
126:
115:
69:
54:
33:acylium ions
32:
26:
467:Acyl groups
57:triple bond
37:carbocation
446:Categories
281:References
143:Reactivity
267:O → R
263:CCO + H
184:CO + AlCl
103:CO + GaCl
76:propionyl
297:(2007),
245:C + CO
180:R + CH
452:Cations
421:Bibcode
275:H + H
116:Acetyl
80:mesityl
18:Acylium
307:
193:→ CH
157:arenes
99:→ CH
305:ISBN
120:and
86:.
78:and
429:doi
393:doi
366:doi
339:doi
271:CCO
229:(CH
197:COC
159:by
155:of
129:C≡O
27:In
448::
427:.
417:28
415:.
389:90
387:.
362:92
360:.
335:28
333:.
318:^
217:.
167::
133:CO
91:CH
67:.
39:.
31:,
435:.
431::
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372:.
368::
345:.
341::
273:2
269:3
265:2
261:3
259:R
243:3
241:)
239:3
235:3
233:)
231:3
207:3
203:4
201:H
199:6
195:3
190:4
187:−
182:3
178:5
176:H
174:6
172:C
109:4
106:−
101:3
97:3
93:3
20:)
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