1,4,8,11-tetraazacyclotetradecane

Also known as 1,4,8,11-tetraazacyclo-tetradecane, cyclam, [14]aneN₄

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. The compound was first prepared by the reaction of 1,3-dibromopropane and ethylenediamine. thumb|left|Structure of one isomer of trans-Ni(cyclam)Cl2. 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

Wikidata facts

Mass: 200.2

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chemical formula: C₁₀H₂₄N₄
canonical SMILES: C1CNCCNCCCNCCNC1
melting point: 186.0
Commons category: Cyclam

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''N''-Alkyl derivatives
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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.