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| - | [[image:Hexachlorostannat(IV)-Ion.svg|thumb|right|Substance which Clorine acts as ligands]]{{otheruses}} ''For [[biochemistry|biochemical]] uses in particular see [[Ligand (biochemistry)]].''
| + | For more information see [http://www.wikipedia.com/wiki/ligands Ligands in Wikipedia] |
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| - | In [[chemistry]], a '''ligand''' is an [[atom]], [[ion]], or [[molecule]] (see also: [[functional group]]) that bond to a central metal, generally involving formal donation of one or more of its [[electron]]s. The metal-ligand bonding ranges from [[covalent bond]] to more ionic. Furthermore, the metal-ligand bond order can range from one to three. Ligands are viewed as a [[Lewis base]] although rare cases are known where [[Lewis acid]]ic ligands serve as electron acceptor.
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| - | All [[metal]] and [[metalloid]]s are bound to ligands in virutally all situations, although gaseous "naked" metal ions can be generated in high vacuum. [[Borane]] BH<sub>3</sub> as ligand for the protection of [[phosphine]] PH<sub>3</sub>),≥ e resulting from the coordination of a ligand (or an array of ligands) to a central atom is termed a [[complex (chemistry)|complex]].
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| - | Factors that characterize the ligands are their charge, size (bulk), and of course the nature of the constituent atoms. Ligands in a complex dictate the [[reactivity]] of the central atom.
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| - | {| class="wikitable"
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| - | == Ligands in metal complexes ==
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| - | In [[coordination chemistry]], the ligands that are directly bonded to the metal (that is, share electrons), are sometimes called "inner sphere" ligands. "Outer-sphere" ligands are not directly attached to the metal, but are bonded, generally weakly, to the first coordination shell, affecting the inner sphere in subtle ways. The complex of the metal with the inner sphere ligands is then called a coordination complex, which can be neutral, cationic, or [[anionic]]). The complex, along with its [[counter ion]]s (if required), is called a [[coordination compound]]. The size of a ligand is indicated by its [[Ligand cone angle|cone angle]].
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| - | ==Donation and back-donation==
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| - | In general, ligands are viewed as donating electrons to the central atom. Bonding is often described using the formalisms of molecular orbital theory. In general, [[Lone electron pair|electron pairs]]) occupy the HOMO of the ligands. In cases where the ligand has low energy LUMO, such orbitals also participate in the bonding and 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 preeminant example a ligand that engages metals via back-donation.
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| - | == Strong field and weak field ligands ==
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| - | {{main|crystal field theory}}
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| - | Ligands and metal ions can be ordered in many ways, one ranking system focuses on ligand 'hardness' (see also [[HSAB theory|hard soft acid base theory]]). Metal ions preferentially bind certain ligands. In general, 'hard' metal ions prefer weak field ligands, whereas 'soft' metal ions prefer strong field ligands. From a [[Molecular orbital theory|MO]] point of view, the [[HOMO/LUMO|HOMO]] of the ligand should have an energy that makes overlap with the LUMO of the metal preferential. Metal ions bound to strong-field ligands follow the [[Aufbau principle]], whereas complexes bound to weak-field ligands follow [[Hund's rule]].
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| - | Binding of the metal with the ligands results in a set of molecular orbitals, where the metal can be identified with a new HOMO and LUMO (the orbitals defining the properties and reactivity of the resulting complex) and a certain ordering of the 5 d-orbitals (which may be filled, or partially filled with electrons). In an [[octahedral]] environment, the 5 otherwise degenerate d-orbitals split in sets of 2 and 3 orbitals (for a more in depth explanation, see [[crystal field theory]]).
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| - | ::3 orbitals of low energy: ''d<sub>xy</sub>'', ''d<sub>xz</sub>'' and ''d<sub>yz</sub>''
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| - | ::2 of high energy: ''d''<sub>''z''<sup>2</sup></sub> and ''d''<sub>''x''<sup>2</sup><nowiki>−</nowiki>''y''<sup>2</sup></sub>
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| - | The energy difference between these 2 sets of d-orbitals is called the splitting parameter, Δ<sub>o</sub>. The magnitude of Δ<sub>o</sub> is determined by the field-strength of the ligand: strong field ligands, by definition, increase Δ<sub>o</sub> more than weak field ligands. Ligands can now be sorted according to the magnitude of Δ<sub>o</sub> (see the table [[Ligand#Examples of common ligands (by field strength)|below]]). This ordering of ligands is almost invariable for all metal ions and is called [[spectrochemical series]].
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| - | For complexes with a tetrahedral surrounding, the d-orbitals again split into two sets, but this time in reverse order:
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| - | ::2 orbitals of low energy: ''d''<sub>''z''<sup>2</sup></sub> and ''d''<sub>''x''<sup>2</sup><nowiki>−</nowiki>''y''<sup>2</sup></sub>
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| - | ::3 orbitals of high energy: ''d''<sub>''xy''</sub>, ''d''<sub>''xz''</sub> and ''d''<sub>''yz''</sub>
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| - | The energy difference between these 2 sets of d-orbitals is now called Δ<sub>t</sub>. The magnitude of Δ<sub>t</sub> is smaller than for Δ<sub>o</sub>, because in a tetrahedral complex only 4 ligands influence the d-orbitals, whereas in an octahedral complex the d-orbitals are influenced by 6 ligands. When the [[coordination number]] is neither octahedral nor tetrahedral, the splitting becomes correspondingly more complex. For the purposes of ranking ligands, however, the properties of the octahedral complexes and the resulting Δ<sub>o</sub> has been of primary interest.
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| - | The arrangement of the d-orbitals on the central atom (as determined by the 'strength' of the ligand), has a strong effect on virtually all the properties of the resulting complexes. E.g. the energy differences in the d-orbitals has a strong effect in the optical absorption spectra of metal complexes. It turns out that valence electrons occupying orbitals with significant 3d-orbital character absorb in the 400-800 nm region of the spectrum (UV-visible range). The absorption of light (what we perceive as the [[color]]) by these electrons (that is, excitation of electrons from one orbital to another orbital under influence of light) can be correlated to the [[ground state]] of the metal complex, which reflects the bonding properties of the ligands. The relative change in (relative) energy of the d-orbitals as a function of the field-strength of the ligands is described in [[Tanabe-Sugano diagram]]s.
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| - | == Ligand bonding motifs and nomenclature ==
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| - | ===Chelation===
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| - | Many ligands are capable of binding metal ion through multiple sites, usually because they have [[lone pair]]s on more than one atom. Ligands that bind via more than one atom are termed ''[[Chelation|chelating]].'' A ligand that binds through two sites is classified as ''bidentate,'' and three sites as ''tridentate.'' The ''bite angle'' refers to the angle between the two bonds of a bidentate chelate. Chelating ligands are commonly formed by linking donor groups via organic linkers. A classic example is [[ethylene diamine]], which is derived by the linking of two ammonia groups with an ethylene (-CH<sub>2</sub>CH<sub>2</sub>-) linker. A classic example of a polydentate ligand is the hexadentate chelating agent [[EDTA]], which is able to bond through six sites, completely surrounding some metals. The number of atoms with which a polydentate ligand bind to the metal centre is called its denticity, symbolized κ<sup>n</sup>, where n indicates the number non-contiguous donor sites by which a ligand attaches to a metal. In practice the n value of a ligand is not indicated explicitly but rather assumed. The binding affinity of a chelating system depends on the chelating angle or [[bite angle]].
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| - | '''[[Hapticity]]''' (η) or eta refers to the number of contiguous atoms in a ligand that are attached to a metal. [[Butadiene]] forms both η<sup>2</sup> and η<sup>4</sup> complexes depending on the number of of carbon atoms are bonded to the metal. [[Cyclopentadienyl]] (Cp) is typically bound in the η<sup>5</sup> mode in which all five carbon atoms are coordinated to the metal. Cp can, however, ring slip to η<sup>3</sup> or η<sup>1</sup> mode in which only three- or one carbon atoms are coordinated to the metal. In this situation the [[Cyclopentadienyl|Cp]] group shifts from the initial 6 electron donor to a 4 or 2 electron donor under the ionic model.
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| - | '''[[Bridging ligand]]s''' link two or more metal centers. Polyatomic ligands such as [[Carbonate|CO<sub>2</sub><sup>2-</sup>]] are especially prone to bridge. The bonding is complicated because polyatomic ligands are ambidentate and thus the capacity for many different [[linkage isomers]]. Atoms that bridge metals are soemtimes indicated with prefix of "μ" (mu). Most inorganic solids, e.g. FeCl<sub>2</sub>, are polymers by virtue of the presence of multiple bridging ligands.
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| - | '''[[linkage isomers|Ambidentate ligand]]''' or polyfunctional ligand can bond to a metal center through different ligand atoms to form various isomers.
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| - | '''[[Noninnocent ligand]]''' is a ligand that bonds with metals in such a manner that the distribution of electron density between the metal center and ligand is unclear. Describing the bonding of noninnocent ligands often involves writing multiple [[Resonance (chemistry)|resonance form]]s which have partial contributions to the overall state.
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| - | '''[[Metal ligand multiple bond]]s''' some ligands can bond to a metal center through the same atom but with a different number of [[lone pair]]s. The [[bond order]] of the metal ligand bond can be in part distinguished through the metal ligand [[bond angle]] (M-X-R). This bond angle is often referred to as being linear or bent with further discussion concerning the degree to which the angle is bent. For example, an imido ligand in the ionic form has three lone pairs. One lone pair is used as a sigma X donor, the other two lone pairs are available as L type pi donors. If both lone pairs are used in pi bonds then the M-N-R geometry is linear. However, if one or both these lone pairs is non-bonding then the M-N-R bond is bent and the extent of the bend speaks to how much pi bonding there may be. η<sup>1</sup>-Nitric oxide can coordinate to a metal center in linear or bent manner.
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| - | ==Hapticity vs denticity==
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| - | [[Hapticity]] (η) and denticity are often confused. Hapticity refers to ''contiguous'' atoms that are attached to a metal. Ethylene forms η<sup>2</sup> complexes because two adjacent carbon atoms bind to the metal. Ethylenediamine forms κ<sup>2</sup> complexes. [[Cyclopentadienyl]] is typically bonded in η<sup>5</sup> mode because all five carbon atoms are bonded to the metal. EDTA<sup>4<nowiki>−</nowiki></sup> on the other hand, when it is sexidentate, is κ<sup>6</sup> mode, the amines and the carboxylate oxygen atoms are not connected directly. To simplify matters, η<sup>n</sup> tends to refer to unsaturated hydrocarbons and κ<sup>n</sup> tends to describe polydentate amine and carboxylate ligands.
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| - | Complexes of polydentate ligands are called ''chelate'' complexes. They tend to be more stable than complexes derived from [[monodentate]] ligands. This enhanced stability is attributed to the necessity to break all of the bonds to the central atom for the hexadentate ligand to be displaced. This increased stability or inertness is called the [[chelate effect]]. In terms of the enhanced thermodynamic stability of chelate complexes, [[entropy]] favors the displacement of many ligands by one polydentate ligand. The increase in the total number of molecules in solution is favorable.
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| - | Related to the chelate effect is the macrocyclic effect. A macrocyclic ligand is any large cyclic ligand which at least partially surrounds the central atom and bonds to it, leaving the central atom at the centre of a large ring. The more rigid and the higher its denticity, the more inert will be the macrocyclic complex. [[Heme]] is a good example, the [[iron]] atom is at the centre of a [[porphyrin]] macrocycle, being bound to four nitrogen atoms of the tetrapyrrole macrocycle. The very stable dimethylglyoximate complex of nickel is a synthetic macrocycle derived from the anion of [[dimethylglyoxime]].
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| - | Unlike polydentate ligands, ambidentate ligands can attach to the central atom in two places but not both. A good example of this is [[thiocyanide]], SCN<sup><nowiki>−</nowiki></sup>, which can attach at either the sulfur atom or the nitrogen atom. Such compounds give rise to [[linkage isomerism]].
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| - | ==Common ligands==
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| - | :''See [[Complex (chemistry)#Naming complexes|nomenclature]].''
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| - | Virtually every molecule and every ion can serve as a ligand for (or "coordinate to") metals. Monodentate ligands include virtually all anions and all simple Lewis bases. Thus, the [[halide]]s and [[pseudohalide]]s are important anionic ligands whereas [[ammonia]], [[carbon monoxide]], and [[water]] are particularly common charge-neutral ligands. Simple organic species are also very common, be they anionic ([[alkoxide|RO<sup><nowiki>−</nowiki></sup>]] and [[Carboxylate|RCO<sub>2</sub><sup><nowiki>−</nowiki></sup>]]) or neutral ([[Ether|R<sub>2</sub>O]], [[Thioether|R<sub>2</sub>S]], [[amine|R<sub>3<nowiki>−</nowiki>x</sub>NH<sub>x</sub>]], and [[phosphine|R<sub>3</sub>P]]). The steric properties of some ligands are evaluated in terms of their [[cone angle]]s.
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| - | Beyond the classical Lewis bases and anions, all unsaturated molecules are also ligands, utilizing their π-electrons in forming the coordinate bond. Also, metals can bind to the σ bonds in for example [[silane]]s, [[hydrocarbon]]s, and [[dihydrogen]] (see also: [[agostic interaction]]).
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| - | In complexes of [[non-innocent ligand]]s, the ligand is bonded to metals via conventional bonds, but the ligand is also redox-active.
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| - | ===Examples of common ligands (by field strength)===<!-- This section is linked from [[Ligand]] -->
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| - | In the following table the ligands are sorted by field strength (weak field ligands first):
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| - | {| class="wikitable" style="margin: 1em auto 1em auto 1em auto 1em auto"
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| - | ! Ligand || formula (bonding atom(s) in bold) || Charge || Most common denticity || Remark(s)
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| - | | [[Iodide]] iodo|| '''I'''<sup><nowiki>−</nowiki></sup> || monoanionic || [[monodentate]] ||
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| - | | [[Bromide]] bromo|| '''Br'''<sup><nowiki>−</nowiki></sup> || monoanionic || monodentate ||
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| - | | [[Sulfide]] thio or bridging thiolate|| '''S'''<sup>2<nowiki>−</nowiki></sup> || dianionic || monodentate (M=S), or bidentate bridging (M-S-M') ||
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| - | | [[Thiocyanate]] thiocyanato|| '''S'''-CN<sup><nowiki>−</nowiki></sup> || monoanionic || monodentate || ambidentate (see also isothiocyanate, ''vide infra'')
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| - | | [[Chloride]] chloro|| '''Cl'''<sup><nowiki>−</nowiki></sup> || monoanionic || monodentate || also found bridging
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| - | | [[Nitrate]] || '''O'''-NO<sub>2</sub><sup><nowiki>−</nowiki></sup> || monoanionic || monodentate ||
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| - | | [[Azide]] || '''N'''-N<sub>2</sub><sup><nowiki>−</nowiki></sup> || monoanionic || monodentate ||
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| - | | [[Fluoride]] fluoro|| '''F'''<sup><nowiki>−</nowiki></sup> || monoanionic || monodentate ||
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| - | | [[Hydroxide]] hydroxo|| '''O'''-H<sup><nowiki>−</nowiki></sup> || monoanionic || monodentate || often found as a bridging ligand
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| - | | [[Oxalate]] || ['''O'''-C(=O)-C(=O)'''-O''']<sup>2<nowiki>−</nowiki></sup> || dianionic || bidentate ||
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| - | | [[Water]] aqua || H-'''O'''-H || neutral || monodentate || monodentate
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| - | | [[Isothiocyanate]] isothiocyanato|| '''N'''=C=S<sup><nowiki>−</nowiki></sup> || monoanionic || monodentate || ambidentate (see also thiocyanate, ''vide supra'')
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| - | | [[Acetonitrile]] || CH<sub>3</sub>C'''N''' || neutral || monodentate ||
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| - | | [[Pyridine]] || C<sub>5</sub>H<sub>5</sub>'''N''' || neutral || monodentate ||
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| - | | [[Ammonia]] ammine|| '''N'''H<sub>3</sub> || neutral || monodentate ||
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| - | | [[Ethylenediamine]] || en || neutral || bidentate ||
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| - | | [[2,2'-Bipyridine]] || bipy || neutral || bidentate || easily reduced to its (radical) anion or even to its dianion
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| - | | 1,10-[[Phenanthroline]] || phen || neutral || bidentate ||
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| - | | [[Nitrite]] nitro or nitrito|| O-N-O<sup><nowiki>−</nowiki></sup> || monoanionic || monodentate || ambidentate
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| - | | [[Triphenylphosphine]] || '''P'''Ph<sub>3</sub> || neutral || monodentate ||
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| - | | [[Cyanide]] cyano|| '''C'''N<sup><nowiki>−</nowiki></sup> || monoanionic || monodentate || can bridge between metals (both metals bound to C, or one to C and one to N)
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| - | | [[Carbon monoxide]] carbonyl || '''C'''O || neutral || monodentate || can bridge between metals (both metals bound to C)
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| - | |}
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| - | Note: The entries in the table are sorted by field strength, binding through the stated atom (i.e. as a terminal ligand), the 'strength' of the ligand changes when the ligand binds in an alternative binding mode (e.g. when it bridges between metals) or when the conformation of the ligand gets distorted (e.g. a linear ligand that is forced through steric interactions to bind in a non-linear fashion).
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| - | === Other general encountered ligands (alphabetical) ===
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| - | In this table other common ligands are listed in alphabetical order.
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| - | {| class="wikitable" style="margin: 1em auto 1em auto 1em auto 1em auto 1em auto"
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| - | ! Ligand || formula (bonding atom(s) in bold) || Charge || Most common denticity || Remark(s)
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| - | | [[Acetylacetone|Acetylacetonate]] (Acac)|| CH<sub>3</sub>-C('''O''')-CH-C('''O''')-CH<sub>3</sub> || monoanionic || bidentate || In general bidentate, bound through both oxygens, but sometimes bound through the central carbon only,<br/> see also analogous ketimine analogues
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| - | | [[Alkene]]s || R<sub>2</sub>'''C=C'''R<sub>2</sub> || neutral || || compounds with a C-C double bond
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| - | | [[Benzene]] || '''C'''<sub>6</sub>H<sub>6</sub> || neutral || || and other arenes
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| - | | [[1,2-Bis(diphenylphosphino)ethane]] (dppe) || Ph<sub>2</sub>'''P'''C<sub>2</sub>H<sub>4</sub>'''P'''Ph<sub>2</sub> || neutral || bidentate ||
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| - | | [[Corrole]]s || || || tetradentate ||
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| - | | [[Crown ether]]s || || neutral || || primarily for alkali and alkaline earth metal cations
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| - | | [[Cryptand|2,2,2-crypt]] || || || hexadentate || primarily for alkali and alkaline earth metal cations
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| - | | [[Cryptate]]s || || neutral || ||
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| - | | [[Cyclopentadienyl complex|Cyclopentadienyl]] || [C<sub>5</sub>H<sub>5</sub>]<sup><nowiki>−</nowiki></sup> || monoanionic || ||
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| - | | [[Diethylenetriamine]] (dien) || || neutral || tridentate || related to TACN, but not constrained to facial complexation
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| - | | [[Dimethylglyoxime|Dimethylglyoximate]] (dmgH<sup><nowiki>−</nowiki></sup>) || || monoanionic || ||
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| - | | [[EDTA|Ethylenediaminetetraacetate]] (EDTA) || || tetra-anionic || hexadentate || actual ligand is the tetra-anion
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| - | | Ethylenediaminetriacetate || || trianionic || pentadentate || actual ligand is the trianion
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| - | | [[Glycine|glycinate]] || || || bidentate || other α-amino acid anions are comparable (but chiral)
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| - | | [[Heme]] || || dianionic || tetradentate || macrocyclic ligand
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| - | | [[Nitrosyl]] || '''N'''O<sup>+</sup> || cationic || || bent (1e) and linear (3e) bonding mode
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| - | | [[Scorpionate ligand]] || || || tridentate ||
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| - | | [[Sulfite]] || || monoanionic || monodentate || ambidentate
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| - | | 2,2',5',2''-[[Terpyridine]] (terpy) || || neutral || tridentate || meridional bonding only
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| - | | [[Thiocyanate]] || || monoanionic || monodentate || ambidentate, sometimes bridging
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| - | | [[Triazacyclononane]] (tacn) || (C<sub>2</sub>H<sub>4</sub>)<sub>3</sub>('''N'''R)<sub>3</sub> || neutral || tridentate || macrocyclic ligand<br/> see also the N,N',N"-trimethylated analogue
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| - | | Tricyclohexylphosphine || (C<sub>6</sub>H<sub>11</sub>)<sub>3</sub>P or (PCy<sub>3</sub>) || neutral || monodentate ||
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| - | | [[Triethylenetetramine]] (trien) || || neutral || tetradentate ||
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| - | | Tri(''o''-tolyl)phosphine || P(''o''-tolyl)<sub>3</sub> || neutral || monodentate ||
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| - | | Tris(2-aminoethyl)amine (tren) || || neutral || tetradentate ||
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| - | | Tris(2-diphenylphosphineethyl)amine (np<sub>3</sub>) || || neutral || tetradentate ||
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| - | |[[Terpyridine]] || || neutral || tridentate ||
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| - | |}
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| - | ==See also==
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| - | *[[2-Mercaptoindole]]
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| - | *[[Crystal field theory]]
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| - | *[[Ligand field theory]]
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| - | *[[Coordination chemistry]]
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| - | *[[Inorganic chemistry]]
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| - | *[[Radioligand]]
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| - | *[[Tanabe-Sugano diagram]]
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| - | *[[Spectrochemical series]]
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| - | *[[Scatchard equation]]
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| - | [[Category:Coordination chemistry]]
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| - | [[Category:Chemical bonding]]
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| - | [[af:Ligand]]
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| - | [[bs:Ligand]]
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| - | [[ca:Lligand]]
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| - | [[cs:Ligand]]
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| - | [[de:Ligand]]
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| - | [[es:Ligando]]
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| - | [[fr:Ligand (chimie)]]
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| - | [[ko:리간드]]
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| - | [[it:Ligando]]
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| - | [[he:ליגנד]]
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| - | [[ja:配位子]]
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| - | [[pl:Ligandy]]
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| - | [[pt:Ligante]]
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| - | [[ru:Лиганд]]
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| - | [[fi:Ligandi (kemia)]]
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| - | [[sv:Ligand]]
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| - | [[th:ลิแกนด์]]
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