307:, is a ground state triplet species with a gap of 30 kcal/mol (130 kJ/mol) to the lowest energy singlet state. Conversely, most arylnitrenium ions are ground state singlets. Certain substituted arylnitrenium ions can be ground state triplets, however. Nitrenium ions can have microsecond or longer lifetimes in water.
329:) bonds. For instance, they are formed upon treatment of chloramine derivatives with silver salts or by activation of aryl hydroxylamine derivatives or aryl azides with Brønsted or Lewis acids. The
399:
465:
Parks, J. M.; Ford, G. P.; Cramer, C. J. (2001). "Quantum chemical characterization of the reactions of guanine with the phenylnitrenium ion".
325:
Nitrenium species have been exploited as intermediates in organic reactions. They are typically generated via heterolysis of N–X (X = N, O,
137:
501:
333:
is an early example of a reaction that is now thought to proceed via an aryl nitrenium intermediate. They can also act as
338:
384:
112:
231:
647:
431:"Reaction of aromatic azides with strong acids: Formation of fused nitrogen heterocycles and arylamines"
652:
318:
oxidation of arylamines. The regiochemistry and energetics of the reaction of phenylnitrenium ion with
330:
58:
556:
260:
98:
513:
8:
517:
78:
537:
310:
Aryl nitrenium ions are of biological interest because of their involvement in certain
16:
Class of reactive intermediate species based on nitrogen and isoeletronic with carbene
626:
578:
541:
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380:
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19:
This article is about the positive ions. For other compounds with the formula NH
225:
429:
de
Carvalho, Marcia; Sorrilha, Ana E. P. M.; Rodrigues, J. Augusto R. (1999).
641:
582:
533:
408:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
292:
284:
213:
24:
417:
486:
334:
478:
573:
557:"Application of Stable Nitrenium Ions to Preparative Organic Chemistry"
176:
89:
375:
Moss, Robert A.; Platz, Matthew S.; Jones, Maitland Jr, eds. (2004).
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322:
has been investigated using density functional theory computations.
224:
Except where otherwise noted, data are given for materials in their
264:
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57:
602:
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28:
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598:"Microwave-assisted generation of carbazolyl nitrenium cation"
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47:
428:
311:
639:
464:
499:
374:
314:damaging processes. They are generated upon
502:"Nitrenium ions: structure and reactivity"
97:
625:
615:
572:
500:Borodkin, G I; Shubin, V G (2008-05-31).
449:
438:Journal of the Brazilian Chemical Society
291:, and can exist in either a singlet or a
554:
640:
595:
124:Key: QTLMMXDMXKCANI-UHFFFAOYSA-N
77:
339:electrophilic aromatic substitution
13:
405:Compendium of Chemical Terminology
14:
664:
169:
163:
526:10.1070/RC2008v077n05ABEH003760
451:10.1590/S0103-50531999000500012
377:Reactive Intermediate Chemistry
228:(at 25 °C , 100 kPa).
589:
548:
493:
458:
422:
393:
368:
1:
361:
617:10.3998/ark.5550190.0002.611
467:Journal of Organic Chemistry
295:. The parent nitrenium ion,
7:
344:
275:and with two substituents (
23:but different charges, see
10:
669:
18:
627:2027/spo.5550190.0002.611
222:
188:
150:
133:
108:
39:
596:Bogdał, Dariusz (2001).
555:Kikugawa, Yasuo (2009).
506:Russian Chemical Reviews
418:10.1351/goldbook.N04146
331:Bamberger rearrangement
648:Reactive intermediates
283:). Nitrenium ions are
267:with both an electron
261:reactive intermediate
121:InChI=1S/H2N/h1H2/q+1
350:The related neutral
518:2008RuCRv..77..395B
184: g·mol
36:
574:10.3987/REV-08-644
232:Infobox references
189:Related compounds
34:
653:Nitrogen hydrides
479:10.1021/jo016066+
473:(26): 8997–9004.
257:organic chemistry
240:Chemical compound
238:
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195:Related compounds
59:Interactive image
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158:Chemical formula
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273:positive charge
255:(obsolete)) in
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84:
64:
51:
32:
22:
17:
12:
11:
5:
666:
656:
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650:
634:
633:
610:(6): 109–115.
588:
547:
512:(5): 395–419.
492:
457:
444:(5): 415–420.
421:
410:nitrenium ions
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385:
366:
365:
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360:
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346:
343:
278:
247:(also called:
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226:standard state
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54:
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35:Nitrenium ion
20:
15:
9:
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3:
2:
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386:9780471233244
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335:electrophiles
332:
328:
323:
321:
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308:
294:
293:triplet state
290:
286:
285:isoelectronic
274:
270:
266:
262:
258:
254:
253:imidonium ion
250:
249:aminylium ion
246:
245:nitrenium ion
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26:
25:amino radical
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601:
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561:Heterocycles
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244:
242:
40:Identifiers
151:Properties
79:CHEBI:29338
642:Categories
567:(3): 571.
362:References
177:Molar mass
90:ChemSpider
46:3D model (
583:0385-5414
542:250845065
534:0036-021X
379:. Wiley.
269:lone pair
263:based on
487:11749633
352:nitrenes
345:See also
289:carbenes
265:nitrogen
603:Arkivoc
514:Bibcode
327:Halogen
320:guanine
316:in vivo
99:4574106
29:azanide
581:
540:
532:
485:
383:
271:and a
182:16.022
138:SMILES
538:S2CID
434:(PDF)
400:IUPAC
287:with
259:is a
113:InChI
70:ChEBI
48:JSmol
608:2001
579:ISSN
530:ISSN
483:PMID
381:ISBN
27:and
622:hdl
612:doi
569:doi
522:doi
475:doi
446:doi
414:doi
412:".
354:R–N
337:in
312:DNA
251:or
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620:.
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600:.
577:.
565:78
563:.
559:.
536:.
528:.
520:.
510:77
508:.
504:.
481:.
471:66
469:.
442:10
440:.
436:.
402:,
341:.
297:NH
243:A
214:NH
212:;
207:NH
205:;
200:NH
630:.
624::
614::
585:.
571::
544:.
524::
516::
489:.
477::
454:.
448::
416::
389:.
356::
303:2
300:+
281:N
279:2
277:R
216:2
209:2
202:4
170:N
167:2
164:H
50:)
31:.
21:2
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