375:
20:
626:
EL Salmawy, M.S., Nakahiro, Y., and
Wakamatsu, T. (1993). The role of silanol group in flotation separation of quartz from feldspar using non-ionic surfactants, 18th IMPC, pp. 845–849, The Australian Institute of Mining and Metallurgical Engineering, Sydney,
134:
are slow to hydrolyze. Compared to the silyl ethers, silyl acetates are faster to hydrolyze, with the advantage that the released acetic acid is less aggressive. For this reason silyl acetates are sometimes recommended for applications.
215:
Silanols are more acidic than the corresponding alcohols. This trend contrasts with the fact that Si is far less electronegative than carbon (1.90 vs 2.55, respectively). For Et
34:
is a functional group in silicon chemistry with the connectivity Si–O–H. It is related to the hydroxy functional group (C–O–H) found in all
260:
is 11. Because of their greater acidity, silanols can be fully deprotonated in aqueous solution, especially the arylsilanols. The conjugate base is called a
532:
Tert-butoxysilanols as model compounds for labile key intermediates of the sol-gel process: crystal and molecular structures of (t-BuO)
439:= 1, 2, 3, 4) are highly unstable and are mainly of interest to theoretical chemists. The perhydroxylated silanol, sometimes called
483:, from Deut. Chem. Ges. Ber., iv, 901 as summarized in "Organic chemistry" J. Chem. Soc., 1872, vol. 25, pp. 133–156.
348:
39:
122:
The hydrolysis of fluorosilanes requires more forcing reagents, i.e. alkali. The alkoxysilanes (
305:
The conversions of silyl halides, acetates, and ethers to siloxanes proceed via silanols. The
156:
102:
of halosilanes, alkoxysilanes, or aminosilanes. Chlorosilanes are the most common reactants:
359:. Organosilanols occur as intermediates in industrial processes such as the manufacturing of
396:
8:
267:
Despite the disparity in acidity, the basicities of alkoxides and siloxides are similar.
159:(for hindered silanes). In the presence of metal catalysts, silanes undergo hydrolysis:
35:
416:
227:
199:
587:
519:
42:
and silicate mineralogy. If a silanol contains one or more organic residues, it is an
640:
440:
332:
583:
563:
543:
515:
484:
464:
195:
68:
24:
343:. Their presence is responsible for the absorption properties of silica gel. In
306:
598:
379:
352:
344:
567:
530:
Beckmann, J.; Dakternieks, D.; Duthie, A.; Larchin, M. L.; Tiekink, E. R. T.:
374:
634:
147:
of hydrosilanes. A wide range of oxidants have been employed including air,
43:
202:. For sterically bulky substituents, even silanetriols have been prepared.
443:, is often discussed in vague terms, but has not been well characterized.
488:
459:
Vadapalli
Chandrasekhar, Ramamoorthy Boomishankar, Selvarajan Nagendran:
392:
123:
364:
356:
99:
468:
391:
Some silanediols and silanetriols inhibit hydrolytic enzymes such as
152:
144:
547:
461:
Recent
Developments in the Synthesis and Structure of Organosilanols
368:
360:
340:
276:
261:
188:
514:, Advances in Inorganic Chemistry Volume 42, 1995, Pages 147–262
148:
407:
Literally, silanol refers to a single compound with the formula
336:
614:
M. Blunder, N. Hurkes, M. List, S. Spirk and R. Pietschnig:
191:. In the solid state, silanols engage in hydrogen-bonding.
93:
347:, derivatization of accessible silanol groups in a bonded
187:
The Si–O bond distance is typically about 1.65
19:
582:, Journal of Chromatography A 1997, volume 779, 29–72.
580:
The silanol group and its role in liquid chromatography
270:
603:
Silanediols: a new class of potent protease inhibitors
618:, Bioorg. Med. Chem. Lett. 2011, volume 21, 363-365.
378:
Trisilanol intermediate in the formation of a cubic
605:, Angew. Chem. Int. Ed. 1998, volume 37, 812-814.
138:
38:. Silanols are often invoked as intermediates in
632:
309:, which entails the conversion of, for example,
512:The Synthesis and Structure of Organosilanols
463:. Chem. Rev. 2004, volume 104, pp 5847–5910.
71:. He prepared the “silicol” by hydrolysis of
59:The first isolated example of a silanol was
194:Most silanols have only one OH group, e.g.
16:Si–OH functional group in silicon chemistry
542:, Appl. Organomet. Chem. 2003, 17, 52–62.
198:. Also known are some silanediols, e.g.,
506:
504:
502:
500:
498:
496:
182:
616:Silanetriols as in vitro AChE Inhibitors
373:
94:From silyl halides and related compounds
18:
601:, T. Nittoli, A. M. Mutahi and L. Guo:
633:
493:
335:, but are pervasive on the surface of
323:, proceeds via silanol intermediates.
98:Silanols are generally synthesized by
54:
560:The Chemistry of Organo Silanetriols
367:in the biodegradation of small ring
363:. Moreover, organosilanols occur as
271:Condensation and the sol-gel process
13:
562:. Coord. Chem. Rev. 2016, 87-106.
402:
14:
652:
226:is estimated at 13.6 vs. 19 for
419:number 14475-38-8). The family
386:
608:
592:
572:
552:
524:
473:
453:
143:An alternative route involves
139:By oxidation of silyl hydrides
49:
1:
588:10.1016/S0021-9673(97)00479-2
520:10.1016/S0898-8838(08)60053-7
446:
326:
558:R. Pietschnig and S. Spirk:
205:
7:
331:Silanols exist not only as
10:
657:
481:On the silicoheptyl series
275:Silanols condense to give
210:
568:10.1016/j.ccr.2016.03.010
355:groups is referred to as
40:organosilicon chemistry
383:
183:Structure and examples
157:potassium permanganate
67:, reported in 1871 by
27:
377:
22:
489:10.1039/JS8722500133
397:acetylcholinesterase
118:Si–OH + HCl
417:Chemical Abstracts
384:
333:chemical compounds
200:diphenylsilanediol
55:From alkoxysilanes
28:
578:Nawrocki, Jacek:
510:Paul D. Lickiss:
469:10.1021/cr0306135
441:orthosilicic acid
264:or a silanolate.
175:Si–OH + H
110:Si–Cl + H
648:
619:
612:
606:
596:
590:
576:
570:
556:
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528:
522:
508:
491:
477:
471:
457:
434:
414:
349:stationary phase
322:
315:
301:
259:
196:trimethylsilanol
167:Si–H + H
133:
89:
78:
69:Albert Ladenburg
66:
25:trimethylsilanol
656:
655:
651:
650:
649:
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645:
631:
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623:
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548:10.1002/aoc.380
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509:
494:
478:
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454:
449:
433:
427:
420:
412:
408:
405:
403:Parent silanols
389:
329:
321:
317:
314:
310:
307:sol-gel process
299:
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273:
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52:
17:
12:
11:
5:
654:
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629:
628:
621:
620:
607:
599:S. M. Sieburth
591:
571:
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537:
533:
523:
492:
479:A. Ladenburg:
472:
451:
450:
448:
445:
429:
422:
410:
404:
401:
388:
385:
380:silsesquioxane
353:trimethylsilyl
345:chromatography
328:
325:
319:
316:into hydrated
312:
303:
302:
297:
293:
289:
285:
272:
269:
255:
251:
247:
243:
237:
231:-butyl alcohol
223:
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209:
207:
204:
184:
181:
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176:
172:
168:
164:
140:
137:
129:
126:) of the type
120:
119:
115:
111:
107:
95:
92:
86:
82:
74:
62:
56:
53:
51:
48:
15:
9:
6:
4:
3:
2:
653:
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158:
154:
150:
146:
136:
125:
105:
104:
103:
101:
91:
70:
47:
45:
44:organosilanol
41:
37:
33:
26:
23:Structure of
21:
615:
610:
602:
594:
579:
574:
559:
554:
531:
526:
511:
480:
475:
460:
455:
436:
430:
424:
406:
390:
387:Biorelevance
371:in mammals.
339:and related
330:
304:
274:
266:
234:
228:
220:
214:
193:
186:
142:
124:silyl ethers
121:
97:
58:
31:
29:
536:SiOH and HO
393:thermolysin
365:metabolites
277:disiloxanes
219:SiOH, the p
50:Preparation
627:Australia.
447:References
357:endcapping
327:Occurrence
288:SiOH → R
153:dioxiranes
100:hydrolysis
369:silicones
361:silicones
341:silicates
206:Reactions
171:O → R
145:oxidation
114:O → R
641:Silanols
635:Category
292:Si−O−SiR
262:siloxide
233:. The p
149:peracids
36:alcohols
311:Si(OEt)
211:Acidity
132:Si(OR')
32:silanol
337:silica
250:)Si(CH
155:, and
79:(Et =
351:with
242:3−ClC
77:SiOEt
428:(OH)
413:SiOH
395:and
229:tert
65:SiOH
584:doi
564:doi
544:doi
516:doi
485:doi
465:doi
421:SiH
318:SiO
296:+ H
284:2 R
240:of
90:).
637::
495:^
423:4−
399:.
279::
258:OH
151:,
73:Et
61:Et
46:.
30:A
586::
566::
546::
540:H
538:2
534:3
518::
487::
467::
437:n
435:(
431:n
425:n
415:(
411:3
409:H
382:.
320:2
313:4
300:O
298:2
294:3
290:3
286:3
256:2
254:)
252:3
248:4
246:H
244:6
238:a
235:K
224:a
221:K
217:3
189:Å
177:2
173:3
169:2
165:3
163:R
130:3
128:R
116:3
112:2
108:3
106:R
87:5
85:H
83:2
81:C
75:3
63:3
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