Cyclam
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| Names | |
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| Preferred IUPAC name
1,4,8,11-Tetraazacyclotetradecane | |
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C10H24N4 | |
| Molar mass | 200.330 g·mol−1 |
| Melting point | 185 to 188 °C (365 to 370 °F; 458 to 461 K) |
| 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).
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Template:Chembox Footer/trackingTemplate:Short description
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]
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.
N-Alkyl derivatives
Metal complexes of cyclam 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 readily prepared by methylation using formaldehyde and formic acid (Eschweiler–Clarke reaction).[1] These oxidatively robust derivatives of cyclam have enabled a number of metal–O2 complexes.[4]
See also
References
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- ^ a b Page Module:Citation/CS1/styles.css has no content.Barefield, E. Kent (2010). "Coordination chemistry of N-tetraalkylated cyclam ligands—A status report". Coord. Chem. Rev. 254 (15–16): 1607–1627. doi:10.1016/j.ccr.2010.03.007.
- ^ Page Module:Citation/CS1/styles.css has no content.Van Alphen, J. (1937). "On Aliphatic Polyamines IV". Recl. Trav. Chim. Pays-Bas. 56 (4): 343–350. doi:10.1002/recl.19370560405.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content.Cho, J.; Sarangi, R.; Nam, W. (2012). "Mononuclear Metal–O2 Complexes Bearing Macrocyclic N-Tetramethylated Cyclam Ligands". Acc. Chem. Res. 45 (8): 1321–1330. doi:10.1021/ar3000019. PMC 3627547. PMID 22612523.
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