Co Dmg 2pyridine Chloride Bf2

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Ball-and-stick model of the tetraamminediaquacopper(II) cation, [Cu(NH3)4(H2O)2]2+

In coordination chemistry, metal ammine complexes are metal complexes containing at least one ammonia (NH3) ligand. 'Ammine' is spelled this way due to historical reasons; in contrast, alkyl or aryl bearing ligands are spelt with a single 'm'. Almost all metal ions bind ammonia as a ligand, but the most prevalent examples of ammine complexes are for Cr(III), Co(III), Ni(II), Cu(II) as well as several platinum group metals.[1]

Co dmg 2 pyridine chloride bf2 10

History[edit]

Structural representations used by Alfred Werner (right) and Sophus Mads Jørgensen for one isomer of the dichloride salt of the complex [Pt(NH3)2(pyridine)2]2+.[2]

Ammine complexes played a major role in the development of coordination chemistry, specifically determination of the stereochemistry and structure. They are easily prepared, and the metal-nitrogen ratio can be determined by elemental analysis. Through studies mainly on the ammine complexes, Alfred Werner developed his Nobel Prize-winning concept of the structure of coordination compounds (see Figure).[3][4]

One of the first ammine complexes to be described was Magnus' green salt, which consists of the platinum tetrammine complex [Pt(NH3)4]2+.[5]

Examples[edit]

Homoleptic poly(ammine) complexes are known for many of the transition metals. Most often, they have the formula [M(NH3)6]n+ where n = 2, 3, and even 4 (M = Pt).[6]

Platinum group metals[edit]

Platinum group metals form diverse ammine complexes. Pentaamine(dinitrogen)ruthenium(II) and the Creutz–Taube complex are well studied examples or historic significance. The complex cis-PtCl2(NH3)2, under the name Cisplatin, is an important anticancer drug. Pentamminerhodium chloride is the dichloride salt of the dicationic pentammine complex [RhCl(NH3)5]2+. This salt is an intermediate in the purification of rhodium from its ores.

  • Metal-Ammine Complexes

  • Carboplatin, a widely used anticancer drug.

  • Pentamminerhodium chloride, the dichloride salt one a cationic pentammine halide complex.

  • Pentaamine(dinitrogen)ruthenium(II)], the first metal dinitrogen complex.

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  • Hexamminecobalt(III) chloride, the trichloride salt of the hexammine complex [Co(NH3)6]3+. It is famously stable in concentrated hydrochloric acid.

    At this year’s conference, Apple announced to the world. Bootable os 10.13 dmg download for laptop.

  • Reinecke's salt features a very stable anionic diamine complex of Cr(III), which is used as a counteranion.

Cobalt(III) and chromium(III)[edit]

The ammines of chromium(III) and cobalt(III) are of historic significance. Both families of ammines are relatively inert kinetically, which allows the separation of isomers.[7] For example, tetraamminedichlorochromium(III) chloride, [Cr(NH3)4Cl2]Cl, has two forms - the cis isomer is violet, while the trans isomer is green. The trichloride of the hexaammine (hexamminecobalt(III) chloride, [Co(NH3)6]Cl3)) exists as only a single isomer. 'Reinecke's salt' with the formula NH4[Cr(NCS)4(NH3)2].H2O was first reported in 1863.[8]

Nickel(II), zinc(II), copper(II)[edit]

Sample of chloropentamminecobalt chloride [CoCl(NH3)5]Cl2, illustrating the vibrant colors typical of transition metal ammine complexes.

Zinc(II) forms a colorless tetraammine with the formula [Zn(NH3)4]2+.[9] Like most zinc complexes, it has a tetrahedral structure. Hexaamminenickel is violet, and the copper(II) complex is deep blue. The latter is characteristic of the presence of copper(II) in qualitative inorganic analysis.

Copper(I), silver(I), and gold(I)[edit]

Copper(I) forms only labile complexes with ammonia, including the trigonal planar [Cu(NH3)3]+.[10] Silver gives the diammine complex [Ag(NH3)2]+ with linear coordination geometry.[11] It is this complex that forms when otherwise rather insoluble silver chloride dissolves in aqueous ammonia. The same complex is the active ingredient in Tollen's reagent. Gold(I) chloride forms a compound with six ammonia, but X-ray crystallography reveals that only two ammonia molecules are ligands.[12]

Reactions[edit]

Ligand exchange and redox reactions[edit]

Since ammonia is a stronger ligand in the spectrochemical series than water, metal ammine complexes are stabilized relative to the corresponding aquo complexes. For similar reasons, metal ammine complexes are less strongly oxidizing than are the corresponding aquo complexes. The latter property is illustrated by the stability of [Co(NH3)6]3+ in aqueous solution and the nonexistence of [Co(H2O)6]3+ (which would oxidize water).

Acid-base reactions[edit]

Once complexed to a metal ion, ammonia is not basic. This property is illustrated by the stability of some metal ammine complexes in strong acid solutions. When the M-NH3 bond is weak, the ammine ligand dissociates and protonation ensues. The behavior is illustrated by the non-reaction and reaction with [Co(NH3)6]3+ and [Ni(NH3)6]2+, respectively.

The ammine ligands are more acidic than is ammonia (pKa ~ 33). For highly cationic complexes such as [Pt(NH3)6]4+, the conjugate base can be obtained. The deprotonation of cobalt(III) ammine-halide complexes, e.g. [CoCl(NH3)5]2+ labilises the Co-Cl bond, according to the Sn1CB mechanism.

Applications[edit]

Metal ammine complexes find many uses. Cisplatin (PtCl2(NH3)2) is a coordination compound containing two chloro and two ammine ligands. This is a drug used in treating cancer.[13] Many other amine complexes of the platinum group metals have been evaluated for this application.

In the separation of the individual platinum metals from their ore, several schemes rely on the precipitation of [RhCl(NH3)5]Cl2. In some separation schemes, palladium is purified by manipulating equilibria involving [Pd(NH3)4]Cl2, PdCl2(NH3)2, and Pt(NH3)4[PdCl4].

In the processing of cellulose, the copper ammine complex known as Schweizer's reagent ([Cu(NH3)4(H2O)2](OH)2) is sometimes used to solubilise the polymer. Schweizer's reagent is prepared by treating an aqueous solutions of copper(II) ions with ammonia. Initially, the light blue hydroxide precipitates only to redissolve upon addition of more ammonia:

[Cu(H2O)6]2+ + 2 OH− → Cu(OH)2 + 6 H2O
Cu(OH)2 + 4 NH3 + 2 H2O → [Cu(NH3)4(H2O)2]2+ + 2 OH−

Silver diammine fluoride ([Ag(NH3)2]F) is a topical medicament (drug) used to treat and prevent dental caries (cavities) and relieve dentinal hypersensitivity.[14]

See also[edit]

References[edit]

  1. ^A. von Zelewsky 'Stereochemistry of Coordination Compounds' John Wiley: Chichester, 1995. ISBN0-471-95599-X.
  2. ^Alfred Werner 'Beitrag zur Konstitution anorganischer Verbindungen' Zeitschrift für anorganische Chemie 1893, Volume 3, pages 267–330.doi:10.1002/zaac.18930030136
  3. ^'Werner Centennial' George B. Kauffman, Ed. Adv. Chem. Ser., 1967, Volume 62. ISBN978-0-8412-0063-0
  4. ^von Zelewsky, A. 'Stereochemistry of Coordination Compounds' John Wiley: Chichester, 1995. ISBN0-471-95599-X.
  5. ^Atoji, M.; Richardson, J. W.; Rundle, R. E. (1957). 'On the Crystal Structures of the Magnus Salts, Pt(NH3)4PtCl4'. J. Am. Chem. Soc.79 (12): 3017–3020. doi:10.1021/ja01569a009.
  6. ^Eßmann, Ralf; Kreiner, Guido; Niemann, Anke; Rechenbach, Dirk; Schmieding, Axel; Sichla, Thomas; Zachwieja, Uwe; Jacobs, Herbert (1996). 'Isotype Strukturen einiger Hexaamminmetall(II)‐halogenide von 3d‐Metallen: [V(NH3)6]I2, [Cr(NH3)6]I2, [Mn(NH3)6]Cl2, [Fe(NH3)6]Cl2, [Fe(NH3)6]Br2, [Co(NH3)6]Br2, und [Ni(NH3)6]Cl2'. Zeitschrift für anorganische und allgemeine Chemie. 622: 1161-1166. doi:10.1002/zaac.19966220709.
  7. ^Basolo, F.; Pearson, R. G. 'Mechanisms of Inorganic Reactions.' John Wiley and Son: New York: 1967. ISBN0-471-05545-X
  8. ^Reinecke, A. 'Über Rhodanchromammonium-Verbindungen' Annalen der Chemie und Pharmacie, volume 126, pages 113-118 (1863). doi: 10.1002/jlac.18631260116.
  9. ^Essmann, R. (1995). 'Influence of coordination on N-H..X- hydrogen bonds. Part 1. [Zn(NH3)4]Br2 and [Zn(NH3)4]I2'. Journal of Molecular Structure. 356: 201–6. Bibcode:1995JMoSt.356.201E. doi:10.1016/0022-2860(95)08957-W.
  10. ^Nilsson, Kersti B.; Persson, Ingmar (2004). 'The coordination chemistry of copper(I) in liquid ammonia, trialkyl and triphenyl phosphite, and tri-n-butylphosphine solution'. Dalton Transactions (9): 1312–1319. doi:10.1039/B400888J.
  11. ^Nilsson, K. B.; Persson, I.; Kessler, V. G. (2006). 'Coordination Chemistry of the Solvated AgI and AuI Ions in Liquid and Aqueous Ammonia, Trialkyl and Triphenyl Phosphite, and Tri-n-butylphosphine Solutions'. Inorganic Chemistry. 45: 6912. doi:10.1021/ic060175v.
  12. ^Scherf, L. M.; Baer, S. A.; Kraus, F.; Bawaked, S. M.; Schmidbaur, H. (2013). 'Implications of the Crystal Structure of the Ammonia Solvate [Au(NH3)2]Cl·4NH3'. Inorganic Chemistry. 52: 2157-2161. doi:10.1021/ic302550q.
  13. ^S. J. Lippard, J. M. Berg 'Principles of Bioinorganic Chemistry' University Science Books: Mill Valley, CA; 1994. ISBN0-935702-73-3.
  14. ^Rosenblatt, A.; Stamford, T. C. M.; Niederman, R. (2009). 'Silver diamine fluoride: a caries 'silver-fluoride bullet''. Journal of Dental Research. 88: 116–125. doi:10.1177/0022034508329406. PMID19278981.CS1 maint: uses authors parameter (link)
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Chloro(pyridine)cobaloxime(III)
Names
Other names
Chloro(pyridine)bis(dimethylglyoximato)cobalt(III), Chloro(N,N'-dihydroxy-2,3-butanediimine-κ2N,N')(N-hydroxy-2,3-butanediiminato-κ2N,N')(methanol)cobalt - pyridine (1:1)
Identifiers
ChemSpider
ECHA InfoCard100.153.977
PubChemCID
CompTox Dashboard(EPA)
  • InChI=1S/2C2H6N2.2ClH.Co/c2*3-1-2-4;;;/h2*3-4H,1-2H2;2*1H;/q2*-2;;;+2/p-2
  • InChI=1S/C9H17N4O4.C5H5N.ClH.Co/c1-6(10)7(2)11-16-19-17-13-9(4)8(3)12-15-18-14-5;1-2-4-6-5-3-1;;/h1-5H3;1-5H;1H;/q-1;;; 2/p-1/b11-7 ,12-8 ,13-9 ;;;
  • CO[H]ON1=C(/C)C(C)=N2O[H]ON3=C(/C)C(C)=N/[Co]123Cl.c1ccccn1
Properties
C13H19ClCoN5O4
Molar mass403.71 g·mol−1
Appearanceyellow-brown solid
insoluble
Hazards
R-phrases(outdated)R36/37/38
S-phrases(outdated)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Chloro(pyridine)cobaloxime is a coordination compound containing a CoIII center with octahedral coordination. It has been considered as a model compound of vitamin B12 for studying the properties and mechanism of action of the vitamin. It belongs to a class of bis(dimethylglyoximato)cobalt(III) complexes with different axial ligands, called cobaloximes.[1] Chloro(pyridine)cobaloxime is a yellow-brown powder that is sparingly soluble in most solvents, including water.

Structure[edit]

The complex adopts a distorted octahedral geometry. Cobalt(III) is bound to two dimethylglyoximate ligands, i.e., mono-deprotonated dimethylglyoxime, in the equatorial plane. Completing the coordination sphere are chloride and a pyridine at the axial positions.[2]

Co Dmg 2 Pyridine Chloride Bf2 Download

Reactions[edit]

The cobaloxime is slowly decomposed by acids and bases. With acids, the products of decomposition are dimethylglyoxime, cobalt salts, and pyridine; with bases, derivatives of other cobaloximes are formed, usually with the release of chloride ions.

Co Dmg 2 Pyridine Chloride Bf2 5

The complex has no reaction with hydrogen gas, and cannot carry oxygen as salcomine does. It would, however, react with hydrogen in the presence of sodium hydroxide, a catalytic amount of platinum metal, or a reduced cobaloxime, therefore once the reduction occurs, the hydrogenation would occur much more rapidly as there is autocatalysis.

The reduction products of cobaloxime depends on the conditions. At pH near 7, a cobaloxime with a CoII center is formed. With a higher pH, the cobalt center would be further reduced to the CoI state, which is supernucleophilic.[3]

Preparation[edit]

The compound is usually prepared by mixing cobalt(II) chloride, dimethylglyoxime and pyridine in an ethanolic solution. This process afford the cobaloxime(II), which is subsequently oxidized by the oxygen in air:[3]

4 CoCl2•6H2O + 8 dmgH2 + 8 py + O2 → 4 ClCo(dmgH)2py + 4 py•HCl + 14 H2O

Co Dmg 2 Pyridine Chloride Bf2 1

Using cobalt(II) acetate in place of cobalt(II) chloride produce aceto(pyridine)cobaloxime. This acetate can be converted to the respective bromide, iodide, cyanate, cyanide, azide and thiocyanate.[3]

(CH3COO)Co(DH)2py + NaX → XCo(DH)2py + NaCH3COO (X = Br, I, CNO, CN, N3 or SCN)

Reactions[edit]

The pyridine base in the axial position can also be replaced by other organic bases containing a sp2 hybridized N atom as well. Commonly used bases are morpholine, 4-methylpyridine, imidazole and benzimidazole. The derivatives are again prepared via diacetocobaloxime, followed by the addition of the desired base, such as imidazole.

(CH3COO)2Co(DH)2 + imi → (CH3COO)Co(DH)2imi

Alkylation of Co[edit]

Chloride

One of the methods used for producing the Co-C bond is to make use of the supernucleophilicity of the CoI center. Chloro(pyridine)cobaloxime(III) is first reduced to Chloro(pyridine)cobaloxime(I) by sodium borohydride in alkaline solution, then an alkyl halide is added into the reaction mixture, and the desired Co-C bond is formed via a SN2 reaction. This method can be used to produce cobaloximes containing a primary or a secondary alkyl substituent.

For derivatives with phenyl or vinyl substituent, the Grignard reaction is employed. However, since the dimethylglyoxime ligands contains two acidic H atoms in the oxime group, the Grignard reagent must be used in three-fold excess to compensate the loss.[3]

References[edit]

  1. ^Jonathan W. Steed; Jerry L. Atwood (2009). Supramolecular Chemistry, 2nd edition. Wiley. p. 808. ISBN978-0-470-51233-3.
  2. ^Geremia, Silvano; Dreos, Renata; Randaccio, Lucio; Tauzher, Giovanni (February 1994). 'Evidence of the interaction between steric and electronic influence in rhodoximes and cobaloximes. Syntehsis of pyRh(DH)2I and X-ray structure of pyRh(DH)2Cl and pyRh(DH)2I'. Inorganica Chimica Acta. Trieste, Italy: Elsevier B.V. 216 (1–2): 125–129. doi:10.1016/0020-1693(93)03708-I.
  3. ^ abcdG. N. Schrauzer (1968). 'Bis(dimethylglyoximato)cobalt complexes (Cobaloximes) - A. Chloro(pyridine)cobaloxime(III)'. Inorganic Syntheses. XI: 62–64. doi:10.1002/9780470132425. ISBN9780470132425.

Co Dmg 2 Pyridine Chloride Bf2 3

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