20:
412:
211:
353:
825:
Keaton, Richard J.; Jayaratne, Kumudini C.; Henningsen, David A.; Koterwas, Lisa A.; Sita, Lawrence R. (2001). "Dramatic
Enhancement of Activities for Living Ziegler−Natta Polymerizations Mediated by "Exposed" Zirconium Acetamidinate Initiators: The Isospecific Living Polymerization of
774:
Alder, Roger W.; Blake, Michael E.; Bufali, Simone; Butts, Craig P.; Orpen, A. Guy; Schütz, Jan; Williams, Stuart J. (2001). "Preparation of tetraalkylformamidinium salts and related species as precursors to stable carbenes".
578:
Roche VF. Improving
Pharmacy Students’ Understanding and Long-term Retention of Acid-Base Chemistry. American Journal of Pharmaceutical Education. 2007;71(6):122.
744:
715:
686:
111:
335:
name). Carboxamidines are frequently referred to simply as amidines, as they are the most commonly encountered type of amidine in
605:
552:
Daniel A. Dickman; Michael Boes; Albert I. Meyers (1989). "(S)-N,N-Dimethyl-N'-(1-tert-Butoxy-3-Methyl-2-Butyl)formamidine".
870:
663:
630:
69:
897:
424:
249:
222:
Several drug or drug candidates feature amidine substituents. Examples include the antiprotozoal
195:
Protonation occurs at the sp-hybridized nitrogen. This occurs because the positive charge can be
597:
590:
192:
Amidines are much more basic than amides and are among the strongest uncharged/unionized bases.
443:— a similar group of compounds where the central carbon atom is bonded to three nitrogen atoms.
257:
253:
135:
115:
196:
8:
261:
248:
Formamidinium (see below) may be reacted with a metal halide to form the light-absorbing
242:
119:
655:
19:
892:
866:
843:
669:
659:
626:
601:
336:
153:
754:
725:
696:
835:
807:
780:
758:
749:
729:
720:
700:
691:
651:
561:
534:
507:
476:
419:
An amidinate salt has the general structure M and can be accessed by reaction of a
131:
39:
35:
24:
798:
Edward C. Taylor; Wendell A. Ehrhart; M. Kawanisi (1966). "Formamidine
Acetate".
320:
99:
428:
379:
234:
886:
811:
797:
753:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
724:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
695:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
565:
551:
538:
511:
480:
415:
Structure of cyclopentadienyl dimethyl zirconium (diisopropyl acetamidinate).
411:
375:
103:
762:
733:
704:
847:
420:
231:
673:
446:
306:
283:
143:
84:
79:
102:. Reaction of the nitrile with alcohol in the presence of acid gives an
352:
299:
256:. Formamidinium (FA) cations or halides may partially or fully replace
238:
147:
74:
839:
784:
440:
223:
123:
276:. The oxoacid from which an amidine is derived must be of the form R
650:. Progress in Medicinal Chemistry. Vol. 30. pp. 203–326.
303:
287:
210:
824:
525:
Arthur C. Hontz, E. C. Wagner (1951). "N,N-Diphenylbenzamidine".
273:
227:
139:
127:
110:
then completes the conversion to the amidine. Instead of using a
107:
431:. They are used widely as ligands in organometallic complexes.
46:, where the R groups can be the same or different. They are the
361:
200:
156:
524:
332:
291:
160:
51:
47:
360:
A notable subclass of amidinium ions are the formamidinium
777:
Journal of the
Chemical Society, Perkin Transactions 1
773:
621:
Schrader, Thomas; Hamilton, Andrew D., eds. (2005).
587:
364:; which can be represented by the chemical formula
589:
382:which can be represented by the chemical formula
58:). The simplest amidine is formamidine, HC(=NH)NH
884:
648:5 Amidines and Guanidines in Medicinal Chemistry
620:
467:A. W. Dox (1928). "Acetamidine Hydrochloride".
865:. Chichester, England: John Wiley & Sons.
207:ion and possesses identical C-N bond lengths.
130:. They are also generated by amination of an
645:
134:. They are also prepared by the addition of
356:general structure of a formamidinium cation
106:. Treatment of the resulting compound with
98:A common route to primary amidines is the
863:Chemistry and technology of carbodiimides
466:
309:, giving amidines the general structure R
260:in forming perovskite absorber layers in
828:Journal of the American Chemical Society
410:
351:
347:
199:onto both nitrogen atoms. The resulting
18:
885:
860:
646:Greenhill, John V.; Lue, Ping (1993).
187:
596:. Oxford university press. p.
13:
750:Compendium of Chemical Terminology
721:Compendium of Chemical Terminology
692:Compendium of Chemical Terminology
406:
272:Formally, amidines are a class of
209:
14:
909:
588:Clayden; Greeves; Warren (2001).
854:
818:
791:
767:
738:
709:
319:. When the parent oxoacid is a
267:
217:
27:of acetamidine (acetimidamide).
680:
639:
623:Functional synthetic receptors
614:
581:
572:
545:
518:
487:
460:
342:
93:
65:Examples of amidines include:
1:
656:10.1016/S0079-6468(08)70378-3
453:
323:, the resulting amidine is a
7:
434:
10:
914:
625:. Wiley-VCH. p. 132.
449:contain a cyclic amidine.
812:10.15227/orgsyn.046.0039
566:10.15227/orgsyn.067.0052
539:10.15227/orgsyn.031.0048
512:10.15227/orgsyn.036.0064
481:10.15227/orgsyn.008.0001
763:10.1351/goldbook.S06107
734:10.1351/goldbook.C00851
705:10.1351/goldbook.A00267
425:organometallic compound
250:semiconducting material
245:at the 5HT2A receptor.
203:species is known as an
861:Ulrich, Henri (2007).
416:
357:
302:group is replaced by =
282:E(=O)OH, where R is a
258:methylammonium halides
254:perovskite solar cells
214:
136:organolithium reagents
28:
498:-Phenylbenzamidine".
414:
355:
348:Formamidinium cations
213:
120:aluminium trichloride
22:
262:photovoltaic devices
159:reacts with primary
826:Vinylcyclohexane".
393:N−C:−NR
226:, the insecticide
188:Acid-base chemistry
122:promote the direct
417:
358:
290:is replaced by an
215:
163:to give amidines:
29:
898:Functional groups
840:10.1021/ja0057326
834:(25): 6197–6198.
800:Organic Syntheses
779:(14): 1586–1593.
607:978-0-19-850346-0
592:Organic chemistry
554:Organic Syntheses
527:Organic Syntheses
500:Organic Syntheses
469:Organic Syntheses
337:organic chemistry
154:Dimethylformamide
36:organic compounds
16:Organic compounds
905:
877:
876:
858:
852:
851:
822:
816:
815:
795:
789:
788:
785:10.1039/B104110J
771:
765:
742:
736:
713:
707:
684:
678:
677:
643:
637:
636:
618:
612:
611:
595:
585:
579:
576:
570:
569:
549:
543:
542:
522:
516:
515:
491:
485:
484:
464:
402:
401:
400:
392:
391:
373:
372:
371:
132:imidoyl chloride
40:functional group
25:skeletal formula
913:
912:
908:
907:
906:
904:
903:
902:
883:
882:
881:
880:
873:
859:
855:
823:
819:
796:
792:
772:
768:
743:
739:
714:
710:
685:
681:
666:
644:
640:
633:
619:
615:
608:
586:
582:
577:
573:
550:
546:
523:
519:
493:
492:
488:
465:
461:
456:
437:
409:
407:Amidinate salts
399:
396:
395:
394:
390:
387:
386:
385:
383:
380:stable carbenes
378:of these gives
370:
368:
367:
366:
365:
350:
345:
329:carboximidamide
321:carboxylic acid
318:
314:
295:
281:
270:
220:
190:
183:NC=NHR + 2 MeOH
182:
178:
174:
170:
100:Pinner reaction
96:
61:
57:
50:derivatives of
45:
17:
12:
11:
5:
911:
901:
900:
895:
879:
878:
871:
853:
817:
790:
766:
755:sulfinamidines
737:
726:carboxamidines
708:
679:
664:
638:
631:
613:
606:
580:
571:
544:
517:
486:
458:
457:
455:
452:
451:
450:
444:
436:
433:
429:methyl lithium
408:
405:
397:
388:
369:
349:
346:
344:
341:
316:
310:
293:
277:
269:
266:
235:tribendimidine
219:
216:
189:
186:
185:
184:
180:
176:
172:
168:
142:, followed by
95:
92:
91:
90:
87:
82:
77:
72:
59:
55:
43:
15:
9:
6:
4:
3:
2:
910:
899:
896:
894:
891:
890:
888:
874:
872:9780470065105
868:
864:
857:
849:
845:
841:
837:
833:
829:
821:
813:
809:
805:
801:
794:
786:
782:
778:
770:
764:
760:
756:
752:
751:
746:
741:
735:
731:
727:
723:
722:
717:
712:
706:
702:
698:
694:
693:
688:
683:
675:
671:
667:
665:9780444899897
661:
657:
653:
649:
642:
634:
632:3-527-30655-2
628:
624:
617:
609:
603:
599:
594:
593:
584:
575:
567:
563:
559:
555:
548:
540:
536:
532:
528:
521:
513:
509:
505:
501:
497:
490:
482:
478:
474:
470:
463:
459:
448:
445:
442:
439:
438:
432:
430:
426:
422:
413:
404:
381:
377:
376:Deprotonation
363:
354:
340:
338:
334:
330:
326:
325:carboxamidine
322:
313:
308:
305:
301:
297:
289:
285:
280:
275:
265:
263:
259:
255:
251:
246:
244:
240:
236:
233:
229:
225:
212:
208:
206:
202:
198:
193:
166:
165:
164:
162:
158:
155:
151:
149:
145:
141:
137:
133:
129:
125:
121:
117:
113:
112:Bronsted acid
109:
105:
101:
88:
86:
83:
81:
78:
76:
73:
71:
68:
67:
66:
63:
53:
49:
41:
37:
33:
26:
21:
862:
856:
831:
827:
820:
803:
799:
793:
776:
769:
748:
740:
719:
711:
690:
682:
647:
641:
622:
616:
591:
583:
574:
557:
553:
547:
530:
526:
520:
506:: 64. 1956.
503:
499:
495:
489:
472:
468:
462:
447:Imidazolines
421:carbodiimide
418:
359:
328:
324:
311:
278:
271:
268:Nomenclature
247:
232:anthelmintic
221:
218:Applications
204:
194:
191:
152:
97:
64:
31:
30:
343:Derivatives
284:substituent
197:delocalized
144:protonation
116:Lewis acids
94:Preparation
85:Pentamidine
80:benzamidine
887:Categories
454:References
441:Guanidines
243:antagonist
239:xylamidine
171:NC(H)(OMe)
148:alkylation
104:iminoether
89:Paranyline
75:diminazene
288:−OH group
224:Imidocarb
205:amidinium
124:amination
38:with the
893:Amidines
848:11414862
697:amidines
435:See also
427:such as
423:with an
315:E(=NR)NR
298:and the
274:oxoacids
201:cationic
140:diimines
128:nitriles
118:such as
54:(RC(O)NR
42:RC(NR)NR
32:Amidines
674:7905649
362:cations
228:amitraz
108:ammonia
869:
846:
806:: 39.
672:
662:
629:
604:
560:: 52.
533:: 48.
286:. The
237:, and
230:, the
161:amines
157:acetal
52:amides
745:IUPAC
716:IUPAC
687:IUPAC
475:: 1.
333:IUPAC
296:group
241:, an
175:+ RNH
48:imine
867:ISBN
844:PMID
670:PMID
660:ISBN
627:ISBN
602:ISBN
179:→ Me
34:are
23:The
836:doi
832:123
808:doi
781:doi
759:doi
757:".
730:doi
728:".
701:doi
699:".
652:doi
598:202
562:doi
535:doi
508:doi
477:doi
327:or
292:−NH
252:in
146:or
138:to
126:of
70:DBU
889::
842:.
830:.
804:46
802:.
747:,
718:,
689:,
668:.
658:.
600:.
558:67
556:.
531:31
529:.
504:36
502:.
471:.
403:.
374:.
339:.
300:=O
264:.
167:Me
150:.
114:,
62:.
875:.
850:.
838::
814:.
810::
787:.
783::
761::
732::
703::
676:.
654::
635:.
610:.
568:.
564::
541:.
537::
514:.
510::
496:N
494:"
483:.
479::
473:8
398:2
389:2
384:R
331:(
317:2
312:n
307:R
304:N
294:2
279:n
181:2
177:2
173:2
169:2
60:2
56:2
44:2
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