106:
The first to postulate a silanone were
Kipping & Lloyd in 1901, but their products were in fact siloxanes. It was not until 2014 that a stable silanone was reported. In this compound, silicon is bonded to a SIDipp
68:
or in the gas phase but not isolated. A synthesis of a stable silanone was reported in 2014. Silanones are of some interest to academic research, with their reactivity being of some relevance to the
338:
Xiong, Y.; Yao, S.; Driess, M. (2013). "Chemical Tricks To
Stabilize Silanones and Their Heavier Homologues with EO Bonds (E=Si–Pb): From Elusive Species to Isolable Building Blocks".
17:
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caused by an unfavorable overlap between the p-orbitals of silicon and oxygen. A second reason for the observed instability is the strongly
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On the proposed thermal interconversion of matrix-isolated dimethylsilylene and 1-methylsilene: their reactions with oxygen atom donors
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180:
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Infrared spectroscopic evidence for silicon-oxygen double bonds: silanone and the silanoic and silicic acid molecules
474:
374:
Sun, T.; Li, J.; Wang, H. (2022). "Recent
Advances in the Chemistry of Heavier Group 14 Analogues of Carbonyls".
301:
F. Stanley
Kipping, Ph.D., D.Sc., F.R.S. and Lorenzo L. Lloyd J. Chem. Soc., Trans., 1901,79, 449-459
178:
Sen, S. S. (2014). "A Stable
Silanone with a Three-Coordinate Silicon Atom: A Century-Long Wait is Over".
376:
88:
260:
M. Bogey; B. Delcroix; A. Walters; J-C Guillemin (1996). "Experimentally
Determined Structure of H
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Silicon–Oxygen Double Bonds: A Stable
Silanone with a Trigonal-Planar Coordinated Silicon Center.
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147:
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Other strategies have recently been used to stabilise silanones, for example coordination to
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8:
420:"An Isolable Silicon Analogue of a Ketone that Contains an Unperturbed Si=O Double Bond"
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Filippou, A. C., Baars, B., Chernov, O., Lebedev, Y. N. and
Schnakenburg, G. (2014),
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XLVII.—Organic derivatives of silicon. Triphenylsilicol and alkyloxysilicon chlorides
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64:(R). Silanones are extremely reactive and until 2013 were only detected by argon
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group. Its stability is owed to the direct coordination of silicon to
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Charles A. Arrington, Robert West, Josef Michl J. Am. Chem. Soc.,
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33:
53:
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Kobayashi, Ryo; Ishida, Shintaro; Iwamoto, Takeaki (2019).
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SiO by
Rotational Spectroscopy and Isotopic Substitution".
16:
136:
139:, in line with expectations. It has been described as a
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239:Robert Withnall, Lester Andrews J. Am. Chem. Soc.,
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119:)imidazolidin-2-ylidene) group and a (Cp)Cr(CO)
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83:. The reason for this instability is the weak
40:. The general description for this class of
52:Si=O, with silicon connected to a terminal
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321:Angew. Chem. Int. Ed., 53: 565–570.
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20:The general structure of a silanone
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75:Silanones are unstable and favor
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1:
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7:
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491:
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220:, 105 (19), pp 6176–6177
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475:Organosilicon compounds
438:10.1002/anie.201905198
389:10.1002/asia.202200611
353:10.1002/anie.201209766
327:10.1002/anie.201308433
286:10.1006/jmsp.1996.0048
193:10.1002/anie.201404793
21:
425:Angew. Chem. Int. Ed.
341:Angew. Chem. Int. Ed.
181:Angew. Chem. Int. Ed.
19:
307:10.1039/CT9017900449
148:Lewis acids or bases
131:. The reported Si=O
89:HOMO–LUMO energy gap
278:1996JMoSp.175..421B
249:10.1021/ja00294a070
226:10.1021/ja00357a048
96:silicon–oxygen bond
383:(18): e202200611.
60:and also with two
22:
431:(28): 9425–9428.
347:(16): 4302–4311.
266:J. Mol. Spectrosc
187:(34): 8820–8822.
143:metallosilanone.
42:organic compounds
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152:steric shielding
129:steric shielding
107:(1,3-bis(2,6-iPr
70:double bond rule
66:matrix isolation
62:organic residues
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133:bond length
58:double bond
56:atom via a
158:References
455:157056381
405:251104394
135:is 1.526
93:polarized
81:siloxanes
30:chemistry
469:Category
447:31095845
397:35883252
361:23450830
201:24990653
141:cationic
125:chromium
98:, Si–O.
26:silanone
274:Bibcode
127:and to
102:History
85:pi bond
34:silicon
32:is the
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359:
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54:oxygen
38:ketone
451:S2CID
401:S2CID
443:PMID
393:PMID
357:PMID
241:1985
218:1983
197:PMID
150:and
44:is R
433:doi
385:doi
349:doi
323:doi
303:doi
282:doi
270:175
245:doi
222:doi
189:doi
79:to
28:in
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345:52
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185:53
166:^
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111:-C
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24:A
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262:2
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191::
137:Ă…
121:3
117:3
115:H
113:6
109:2
50:2
48:R
46:1
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