261:
186:
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571:
408:
24:
706:
Scott, Brian; Brewer, Karen J.; Spreer, Larry O.; Craig, Carl A.; Otvos, John W.; Calvin, Melvin; Taylor, Scott (1990). "A Novel
Conformation for a Coordinated Macrocycle: The Crystal Structure of [Ni(12-aneN
421:
761:
Gunnlaugsson, Thorfinnur; Leonard, Joseph P. (2005). "Responsive lanthanide luminescent cyclen complexes: From switching/Sensing to supramolecular architectures".
310:
558:
827:
Barraza, Ramiro; Sertage, Alexander G.; Kajjam, Aravind B.; Ward, Cassandra L.; Lutter, Jacob C.; Schlegel, H. Bernhard; Allen, Matthew J. (2022).
529:
High dilution conditions result in a low reaction rate penalty and this disadvantage is removed in an alternative procedure starting from
792:
Joshi, Tanmaya; Graham, Bim; Spiccia, Leone (2015). "Macrocyclic Metal
Complexes for Metalloenzyme Mimicry and Sensor Development".
275:
611:
930:
582:
428:
218:
829:"Properties of Amine-Containing Ligands That Are Necessary for Visible-Light-Promoted Catalysis with Divalent Europium"
239:
610:
Lejault, Pauline; Duskova, Katerina; Bernhard, Claire; Valverde, Ibai E.; Romieu, Anthony; Monchaud, David (2019).
935:
925:
581:
of cyclen have been studied extensively. With a 12-membered ring, it tends to bind to four contiguous sites on
915:
181:
530:
143:
920:
578:
476:
36:
256:
589:
ligand tens to form attach to four coplanar sites. It also forms complexes of the type where Ln =
479:
to facilitate ring-formation. Illustrative is the reaction of the deprotonated tosylamides with di
62:
886:
634:
103:
96:
858:
809:
774:
652:
Atkins, T. J.; Richman, J. E.; Oettle, W. F. (1978). "1,4,7,10,13,16-Hexaazacyclooctadecane".
546:
894:
848:
840:
801:
766:
743:
688:
661:
626:
338:
227:
163:
448:
526:
The resulting macrocycle can be deprotected with strong acid. Base gives the tetramine.
72:
260:
185:
123:
853:
828:
464:
399:
909:
638:
542:
534:
387:
174:
574:
Structure of . Color code: O = red, N = blue, Ni = dark blue, white = H, gray = C.
844:
207:
805:
747:
590:
366:
154:
692:
665:
570:
898:
862:
813:
778:
679:
Reed, David P.; Weisman, Gary R. (2002). "1,4,7,10-Tetraazacyclododecane".
630:
612:"The Scope of Application of Macrocyclic Polyamines Beyond Metal Chelation"
480:
538:
194:
770:
586:
134:
463:. It is a white solid. Being structurally simple, symmetrical, and
398:
Except where otherwise noted, data are given for materials in their
569:
550:
114:
102:
95:
85:
23:
880:
Suchý, M.; Hudson, R. H. E. (2008). "Synthetic
Strategies Toward
244:
284:
InChI=1S/C8H20N4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h9-12H,1-8H2
294:
InChI=1/C8H20N4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h9-12H,1-8H2
416:
392:110–113 °C (230–235 °F; 383–386 K)
206:
71:
8:
259:
184:
162:
15:
852:
226:
602:
467:, cyclen has been widely investigated.
315:
280:
255:
175:
619:European Journal of Organic Chemistry
287:Key: QBPPRVHXOZRESW-UHFFFAOYSA-N
142:
122:
7:
734:= 1,4,7,10-Tetraazacyclododecane)".
297:Key: QBPPRVHXOZRESW-UHFFFAOYAQ
197:
14:
736:Journal of Coordination Chemistry
557:
406:
356:
350:
22:
402:(at 25 °C , 100 kPa).
445:1,4,7,10-tetraazacyclododecane
344:
1:
845:10.1021/acs.inorgchem.2c02911
794:Accounts of Chemical Research
41:1,4,7,10-Tetrazacyclododecane
806:10.1021/acs.accounts.5b00142
475:Some syntheses exploit the
952:
884:-Functionalized Cyclens".
748:10.1080/00958979009408193
585:. In contrast the larger
396:
331:
306:
271:
55:
47:
35:
30:
21:
693:10.15227/orgsyn.078.0073
666:10.15227/orgsyn.058.0086
549:and ring expansion with
763:Chemical Communications
583:octaheral metal centers
899:10.1002/ejoc.200800636
631:10.1002/ejoc.201900870
579:Coordination complexes
575:
566:Coordination complexes
931:Nitrogen heterocycles
573:
531:triethylenetetraamine
477:Thorpe-Ingold effect
451:with the formula (CH
37:Preferred IUPAC name
839:(49): 19649–19657.
833:Inorganic Chemistry
374: g·mol
50:Tetraaza-12-crown-4
18:
887:Eur. J. Org. Chem.
576:
429:Infobox references
16:
893:(29): 4847–4865.
765:(25): 3114–3131.
625:(36): 6146–6157.
437:Chemical compound
435:
434:
240:CompTox Dashboard
104:Interactive image
97:Interactive image
943:
936:Secondary amines
926:Chelating agents
902:
867:
866:
856:
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818:
817:
800:(8): 2366–2379.
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783:
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771:10.1039/b418196d
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545:) – followed by
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339:Chemical formula
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874:Further reading
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449:aza-crown ether
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916:Ethyleneamines
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742:(4): 307–313.
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400:standard state
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323:C1CNCCNCCNCCN1
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318:N1CCNCCNCCNCC1
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257:DTXSID60183621
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541:– also a bis(
540:
536:
535:dithiooxamide
532:
527:
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388:Melting point
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176:ECHA InfoCard
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440:
439:
382:White solid
56:Identifiers
48:Other names
921:Macrocycles
730:O; (12-aneN
543:imidazoline
379:Appearance
332:Properties
182:100.102.391
144:ChEMBL19880
124:CHEBI:37391
910:Categories
681:Org. Synth
654:Org. Synth
597:References
591:lanthanide
539:bisamidine
367:Molar mass
228:964584YO2O
155:ChemSpider
84:3D model (
63:CAS Number
718:](CIO
639:201220297
547:reduction
511:→ (TsNCH
499:+ TsN(CH
481:tosylates
471:Synthesis
863:36417708
814:26244894
779:15968347
73:294-90-6
854:9771976
447:) is a
422:what is
420: (
372:172.276
195:PubChem
17:Cyclen
861:
851:
812:
777:
687:: 73.
660:: 86.
637:
587:cyclam
495:NTsNa)
487:TsN(CH
441:Cyclen
417:verify
414:
311:SMILES
135:ChEMBL
31:Names
635:S2CID
615:(PDF)
551:DIBAL
537:to a
276:InChI
208:64963
164:58488
115:ChEBI
86:JSmol
891:2008
859:PMID
810:PMID
775:PMID
710:)(OH
623:2019
533:and
507:OTs)
219:UNII
895:doi
849:PMC
841:doi
802:doi
767:doi
744:doi
689:doi
662:doi
627:doi
459:NH)
245:EPA
198:CID
912::
857:.
847:.
837:61
835:.
831:.
808:.
798:48
796:.
773:.
740:21
738:.
726:·H
685:78
683:.
658:58
656:.
633:.
621:.
617:.
593:.
553:.
515:CH
503:CH
491:CH
483::
455:CH
354:20
901:.
897::
882:N
865:.
843::
816:.
804::
781:.
769::
750:.
746::
732:4
728:2
724:2
722:)
720:4
716:2
714:)
712:2
708:4
695:.
691::
668:.
664::
641:.
629::
521:4
519:)
517:2
513:2
509:2
505:2
501:2
497:2
493:2
489:2
461:4
457:2
453:2
443:(
412:Y
360:4
357:N
351:H
348:8
345:C
247:)
243:(
88:)
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