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Ethylenediamine ligand chelating to a metal with two bonds Cu 2+ complexes with nonchelating methylamine (left) and chelating ethylenediamine (right) ligands. The chelate effect is the greater affinity of chelating ligands for a metal ion than that of similar nonchelating (monodentate) ligands for the same metal.
This ligand–metal–ligand geometric parameter is used to classify chelating ligands, including those in organometallic complexes. It is most often discussed in terms of catalysis , as changes in bite angle can affect not just the activity and selectivity of a catalytic reaction but even allow alternative reaction pathways to become accessible.
Most commonly, amino acids coordinate to metal ions as N,O bidentate ligands, utilizing the amino group and the carboxylate. They are "L-X" ligands. A five-membered chelate ring is formed. The chelate ring is only slightly ruffled at the sp 3-hybridized carbon and nitrogen centers.
The metal–ligand bond can be further stabilised by a formal donation of electron density back to the ligand in a process known as back-bonding. In this case a filled, central-atom-based orbital donates density into the LUMO of the (coordinated) ligand. Carbon monoxide is the preeminent example a ligand that engages metals via back-donation.
The chelate effect increases as the number of chelate rings increases. For example, the complex [Ni(dien) 2)] 2+ is more stable than the complex [Ni(en) 3)] 2+; both complexes are octahedral with six nitrogen atoms around the nickel ion, but dien (diethylenetriamine, 1,4,7-triazaheptane) is a tridentate ligand and en is bidentate. The number of ...
Ethylenediamine is a well-known bidentate chelating ligand for coordination compounds, with the two nitrogen atoms donating their lone pairs of electrons when ethylenediamine acts as a ligand. It is often abbreviated "en" in inorganic chemistry. The complex [Co(en) 3] 3+ is a well studied example. Schiff base ligands easily form from ...
A common diphosphine ligand is dppe, which forms a five-membered chelate ring with most metals. Some diphosphines, such as the extraordinary case of t Bu 2 P(CH 2 ) 10 P t Bu 2 , give macrocyclic complexes with as many as 72 atoms in a ring.
DOTA is derived from the macrocycle known as cyclen.The four secondary amine groups are modified by replacement of the N-H centers with N-CH 2 CO 2 H groups. The resulting aminopolycarboxylic acid, upon ionization of the carboxylic acid groups, is a high affinity chelating agent for di- and trivalent cations.