Cyclam

Cyclam
Names
	Preferred IUPAC name 1,4,8,11-Tetraazacyclotetradecane
Identifiers
CAS Number	295-37-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:37401 ;
ChEMBL	ChEMBL125150 ;
ChemSpider	58489 ;
ECHA InfoCard	100.005.491
PubChem CID	64964;
UNII	EP5AZ544VP ;
CompTox Dashboard (EPA)	DTXSID30183698 ;
	InChI InChI=1S/C10H24N4/c1-3-11-7-9-13-5-2-6-14-10-8-12-4-1/h11-14H,1-10H2 Key: MDAXKAUIABOHTD-UHFFFAOYSA-N ;
	SMILES N1CCNCCCNCCNCCC1;
Properties
Chemical formula	C10H24N4
Molar mass	200.330 g·mol−1
Melting point	185 to 188 °C (365 to 370 °F; 458 to 461 K)
Solubility in water	5 g/100 mL (20 °C)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cyclam (1,4,8,11-tetraazacyclotetradecane) is an organic compound with the formula (NHCH₂CH₂NHCH₂CH₂CH₂)₂. Classified as an aza-crown ether, it is a white solid that is soluble in water. As a macrocyclic ligand, it binds strongly to many transition metal cations.^[1] The compound was first prepared by the reaction of 1,3-dibromopropane and ethylenediamine.^[2]

Structure of one isomer of *trans*-Ni(cyclam)Cl₂.^[3]

The compound features four secondary amines. Its complexes therefore can exist as several diastereomers, depending on the relative orientation of the N–H centres. Its complexes feature alternating five- and six-membered chelate rings. The closely related ligand cyclen ((CH₂CH₂NH)₄) forms only five-membered C₂N₂M chelate rings and tends not to form square-planar complexes.

^ Cite error: The named reference Barefield was invoked but never defined (see the help page).
^ Van Alphen, J. (1937). "On Aliphatic Polyamines IV". Recl. Trav. Chim. Pays-Bas. 56 (4): 343–350. doi:10.1002/recl.19370560405.
^ Ito, T.; Kato, M.; Ito, H. (1984). "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-NiX₂N₄ Type". Bull. Chem. Soc. Jpn. 57 (9): 2641. doi:10.1246/bcsj.57.2641.

[Barefield-1] Cite error: The named reference Barefield was invoked but never defined (see the help page).

[2] Van Alphen, J. (1937). "On Aliphatic Polyamines IV". Recl. Trav. Chim. Pays-Bas. 56 (4): 343–350. doi:10.1002/recl.19370560405.

[3] Ito, T.; Kato, M.; Ito, H. (1984). "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-NiX₂N₄ Type". Bull. Chem. Soc. Jpn. 57 (9): 2641. doi:10.1246/bcsj.57.2641.

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