page_title: Cyclam
section_title: N-Alkyl derivatives
hierarchical_section_title: Cyclam / N-Alkyl derivatives
caption_attribution_description: English: 5 diastereomers of M(cyclam)
context_page_description: Cyclam 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.
  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 forms only five-membered C₂N₂M chelate rings and tends not to form square-planar complexes.
context_section_description: 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.
caption: Isomers of a square planar metal cyclam complex.
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