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648:"The Structures of trans-Dichloro- and trans-Bis(isothiocyanato)nickel(II) Complexes with 1,4,8,11-Tetraazacyclotetradecane, 1,4,8,12-Tetraazacyclopentadecane, and 1,5,9,13-Tetraazacyclohexadecane. The Negative Correlation between the Axial and In-plane Coordination Bond Lengths in Tetragonal Ni(II) Complexes of the trans-NiX
530:
Metal-cyclam complexes are prone to oxidative degradation, which is initiated by deprotonation of the secondary amine. This flaw led to the development of cyclam derivatives wherein the NH centres are replaced by tertiary amines. For example, the tetramethyl derivatives (tetramethylcyclam, tmc) are
395:
495:, depending on the relative orientation of the N–H centres. Its complexes feature alternating five- and six-membered chelate rings. The closely related ligand
285:
260:
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and formic acid. These oxidatively robust derivatives of cyclam have enabled a number of
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Except where otherwise noted, data are given for materials in their
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InChI=1S/C10H24N4/c1-3-11-7-9-13-5-2-6-14-10-8-12-4-1/h11-14H,1-10H2
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470:
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M chelate rings and tends not to form square-planar complexes.
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354:
185 to 188 °C (365 to 370 °F; 458 to 461 K)
390:
588:
Barefield, E. Kent (2010). "Coordination chemistry of
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Van Alphen, J. (1937). "On
Aliphatic Polyamines IV".
460:. The compound was first prepared by the reaction of
449:, it is a white solid that is soluble in water. As a
592:-tetraalkylated cyclam ligands—A status report".
550:Isomers of a square planar metal cyclam complex.
491:. Its complexes therefore can exist as several
191:
63:
456:, it binds strongly to many transition metal
8:
583:
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417:(1,4,8,11-tetraazacyclotetradecane) is an
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15:
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211:
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687:Cho, J.; Sarangi, R.; Nam, W. (2012).
531:readily prepared by methylation using
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272:Key: MDAXKAUIABOHTD-UHFFFAOYSA-N
127:
107:
7:
646:Ito, T.; Kato, M.; Ito, H. (1984).
182:
14:
41:1,4,8,11-Tetraazacyclotetradecane
697:-Tetramethylated Cyclam Ligands"
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326:
320:
22:
376:(at 25 °C , 100 kPa).
693:Complexes Bearing Macrocyclic
314:
1:
511:) forms only five-membered C
487:The compound features four
475:Structure of one isomer of
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621:Recl. Trav. Chim. Pays-Bas
606:10.1016/j.ccr.2010.03.007
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301:
281:
256:
47:
35:
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21:
633:10.1002/recl.19370560405
366:5 g/100 mL (20 °C)
551:
484:
421:with the formula (NHCH
751:Nitrogen heterocycles
549:
474:
689:"Mononuclear Metal–O
673:10.1246/bcsj.57.2641
660:Bull. Chem. Soc. Jpn
600:(15–16): 1607–1627.
37:Preferred IUPAC name
445:. Classified as an
361:Solubility in water
344: g·mol
18:
552:
526:-Alkyl derivatives
485:
462:1,3-dibromopropane
403:Infobox references
16:
713:10.1021/ar3000019
411:Chemical compound
409:
408:
225:CompTox Dashboard
89:Interactive image
778:
771:Chelating agents
756:Secondary amines
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707:(8): 1321–1330.
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594:Coord. Chem. Rev
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489:secondary amines
419:organic compound
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309:Chemical formula
293:N1CCNCCCNCCNCCC1
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466:ethylenediamine
447:aza-crown ether
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627:(4): 343–350.
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374:standard state
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493:diastereomers
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479:-Ni(cyclam)Cl
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561:Sarcophagine
533:formaldehyde
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129:ChEMBL125150
48:Identifiers
761:Macrocycles
666:(9): 2641.
451:macrocyclic
302:Properties
167:100.005.491
109:CHEBI:37401
766:Polyamines
745:Categories
572:References
566:Plerixafor
337:Molar mass
213:EP5AZ544VP
140:ChemSpider
76:3D model (
55:CAS Number
541:complexes
731:22612523
555:See also
65:295-37-4
722:3627547
537:metal–O
458:cations
396:what is
394: (
342:200.330
180:PubChem
17:Cyclam
729:
719:
497:cyclen
454:ligand
415:Cyclam
391:verify
388:
286:SMILES
120:ChEMBL
31:Names
656:Type"
477:trans
261:InChI
193:64964
149:58489
100:ChEBI
78:JSmol
727:PMID
499:((CH
464:and
429:NHCH
204:UNII
717:PMC
709:doi
668:doi
629:doi
602:doi
598:254
507:NH)
230:EPA
183:CID
747::
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703:.
699:.
664:57
662:.
658:.
625:56
623:.
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580:^
543:.
503:CH
468:.
437:CH
433:CH
425:CH
324:24
318:10
733:.
711::
695:N
691:2
676:.
670::
654:4
652:N
650:2
635:.
631::
608:.
604::
590:N
539:2
524:N
517:2
515:N
513:2
509:4
505:2
501:2
483:.
481:2
443:2
441:)
439:2
435:2
431:2
427:2
423:2
386:N
330:4
327:N
321:H
315:C
232:)
228:(
80:)
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