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Cyclam

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Formula
  
C10H24N4

Cyclam httpsuploadwikimediaorgwikipediacommons22

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

Contents

Cyclam Cyclam Wikipedia

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.

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N-Alkyl derivatives

Cyclam Cyclam 14811tetraazacyclotetradecane synthesis

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 are readily prepared by methylation using formaldehyde and formic acid. These oxidatively robust derivatives of cyclam have enabled a number of metal–O2 complexes.


Cyclam 14811Tetraazacyclotetradecane 98 GC SigmaAldrich

References

Cyclam Wikipedia