37:
505:
321:. Normal bases are also nucleophiles, but often chemists seek the proton-removing ability of a base without any other functions. Typical non-nucleophilic bases are bulky, such that protons can attach to the basic center but
36:
542:
Rafael R. Kostikov, Sánchez-Sancho
Francisco, MarĂa Garranzo and M. Carmen Murcia "2,6-Di-t-butylpyridine" Encyclopedia of Reagents for Organic Synthesis 2010.
229:
170:
290:
17:
427:
372:
587:
423:
433:
283:
358:
362:
448:. These compounds are dense, salt-like materials that are insoluble and operate by surface reactions.
378:
341:
61:
480:
412:
276:
126:
111:
106:
464:
455:
of conjugate acid around 17) but of modest but not negligible nucleophilicity. Examples include
131:
308:
249:
56:
234:
175:
141:
101:
91:
526:
K. L. Sorgi, "Diisopropylethylamine," Encyclopedia of
Reagents for Organic Synthesis, 2001.
496:
456:
136:
8:
570:
559:
Activation in anionic polymerization: Why phosphazene bases are very exciting promoters
333:
A variety of amines and nitrogen heterocycles are useful bases of moderate strength (pK
404:
Non-nucleophilic bases of high strength are usually anions. For these species, the pK
445:
146:
566:
543:
527:
314:
311:
219:
81:
71:
547:
121:
86:
46:
441:
511:
This reaction (deprotonation with LDA) is commonly used to generate enolates.
581:
531:
484:
66:
239:
190:
185:
180:
96:
388:
318:
244:
195:
76:
322:
210:
264:
254:
205:
200:
151:
504:
392:
488:
492:
160:
51:
116:
499:, instead of undergoing a nucleophilic substitution.
479:The following diagram shows how the hindered base,
579:
284:
408:s of the conjugate acids are around 35–40.
291:
277:
328:
440:Other strong non-nucleophilic bases are
561:S. Boileau, N. Illy Prog. Polym. Sci.,
14:
580:
451:Some reagents are of high basicity (pK
351:(DIPEA, also called HĂĽnig's Base), pK
24:
571:10.1016/j.progpolymsci.2011.05.005
428:potassium bis(trimethylsilyl)amide
25:
599:
381:, a weak non-nucleophilic base pK
503:
430:(NaHMDS and KHMDS, respectively)
373:1,5-Diazabicyclo(4.3.0)non-5-ene
337:of conjugate acid around 10-13)
35:
325:and complexation is inhibited.
552:
536:
520:
422:Silicon-based amides, such as
13:
1:
548:10.1002/047084289X.rd068.pub2
514:
434:Lithium tetramethylpiperidide
7:
359:1,8-Diazabicycloundec-7-ene
10:
604:
497:Claisen ester condensation
474:
379:2,6-Di-tert-butylpyridine
375:(DBN) - comparable to DBU
18:Sterically hindered bases
532:10.1002/047084289X.rd254
481:lithium diisopropylamide
413:Lithium diisopropylamide
363:E2 elimination reactions
303:As the name suggests, a
127:Self-ionization of water
112:Hammett acidity function
436:(LiTMP or harpoon base)
588:Non-nucleophilic bases
349:-Diisopropylethylamine
329:Non-nucleophilic bases
305:non-nucleophilic base
142:Frustrated Lewis pair
102:Equilibrium chemistry
92:Dissociation constant
62:Acid–base homeostasis
137:Lewis acid catalysis
361:(DBU) - useful for
309:sterically hindered
57:Acid–base reaction
565:, 36, 1132-1151,
446:potassium hydride
389:Phosphazene bases
301:
300:
147:Chiral Lewis acid
16:(Redirected from
595:
573:
556:
550:
540:
534:
524:
507:
293:
286:
279:
260:Non-nucleophilic
87:Buffer solutions
72:Acidity function
39:
27:
26:
21:
603:
602:
598:
597:
596:
594:
593:
592:
578:
577:
576:
557:
553:
541:
537:
525:
521:
517:
477:
454:
418:
407:
399:
384:
368:
354:
336:
331:
317:that is a poor
297:
122:Proton affinity
47:Acceptor number
30:Acids and bases
23:
22:
15:
12:
11:
5:
601:
591:
590:
575:
574:
551:
535:
518:
516:
513:
509:
508:
476:
473:
452:
442:sodium hydride
438:
437:
431:
420:
416:
405:
402:
401:
397:
386:
382:
376:
370:
366:
356:
352:
334:
330:
327:
299:
298:
296:
295:
288:
281:
273:
270:
269:
268:
267:
262:
257:
252:
247:
242:
237:
232:
230:Brønsted–Lowry
224:
223:
216:
215:
214:
213:
208:
203:
198:
193:
188:
183:
178:
173:
171:Brønsted–Lowry
165:
164:
157:
156:
155:
154:
149:
144:
139:
134:
129:
124:
119:
114:
109:
104:
99:
94:
89:
84:
79:
74:
69:
64:
59:
54:
49:
41:
40:
32:
31:
9:
6:
4:
3:
2:
600:
589:
586:
585:
583:
572:
568:
564:
560:
555:
549:
545:
539:
533:
529:
523:
519:
512:
506:
502:
501:
500:
498:
494:
490:
486:
483:, is used to
482:
472:
470:
468:
462:
460:
449:
447:
443:
435:
432:
429:
425:
421:
414:
411:
410:
409:
400:
395:
390:
387:
380:
377:
374:
371:
364:
360:
357:
350:
348:
344:
340:
339:
338:
326:
324:
320:
316:
313:
310:
306:
294:
289:
287:
282:
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274:
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271:
266:
263:
261:
258:
256:
253:
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246:
243:
241:
238:
236:
233:
231:
228:
227:
226:
225:
221:
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217:
212:
209:
207:
204:
202:
199:
197:
194:
192:
189:
187:
184:
182:
179:
177:
174:
172:
169:
168:
167:
166:
162:
159:
158:
153:
150:
148:
145:
143:
140:
138:
135:
133:
130:
128:
125:
123:
120:
118:
115:
113:
110:
108:
105:
103:
100:
98:
95:
93:
90:
88:
85:
83:
80:
78:
75:
73:
70:
68:
67:Acid strength
65:
63:
60:
58:
55:
53:
50:
48:
45:
44:
43:
42:
38:
34:
33:
29:
28:
19:
562:
558:
554:
538:
522:
510:
491:to give the
478:
466:
458:
450:
439:
403:
393:
346:
342:
332:
304:
302:
259:
97:Donor number
485:deprotonate
319:nucleophile
77:Amphoterism
515:References
465:potassium
391:, such as
323:alkylation
255:Superbases
201:Superacids
107:Extraction
469:-butoxide
461:-butoxide
415:(LDA), pK
152:ECW model
132:Titration
582:Category
495:in the
493:enolate
475:Example
457:sodium
355:= 10.75
312:organic
240:Organic
186:Organic
181:Mineral
424:sodium
385:= 3.58
369:= 13.5
250:Strong
196:Strong
489:ester
396:-Bu-P
307:is a
245:Oxide
235:Lewis
222:types
211:Solid
191:Oxide
176:Lewis
163:types
563:2011
467:tert
463:and
459:tert
444:and
426:and
419:= 36
365:, pK
315:base
265:Weak
220:Base
206:Weak
161:Acid
82:Base
52:Acid
567:doi
544:doi
528:doi
487:an
584::
471:.
117:pH
569::
546::
530::
453:a
417:a
406:a
398:4
394:t
383:a
367:a
353:a
347:N
345:,
343:N
335:a
292:e
285:t
278:v
20:)
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