Vanadyl acetylacetonate

Names
IUPAC name

oxobis(2,4-pentanedionato)vanadium(IV)

Other names

VO(acac)2, VO(pd)2

Identifiers

CAS Number

* 3153-26-2 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 17344686

ECHA InfoCard | 100.019.628
EC Number |

* 221-590-8

PubChem CID

* 16217092

CompTox Dashboard (EPA)

* DTXSID70904369

SMILES

* CC(=[O+]1)C=C(C)O[V-3]12(#[O+])OC(C)=CC(C)=[O+]2

Properties

Chemical formula

| C10H14O5V
Molar mass | 265.157 g/mol
Appearance  | blue-green
Density | 1.50 g/cm3
Melting point | 258 °C (496 °F; 531 K)
Boiling point | 174 °C (345 °F; 447 K) at 0.2 torrs (27 Pa)

Solubility in water

| CHCl3, CH2Cl2, Benzene, CH3OH, CH3CH2OH

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)

Infobox references

Chemical compound

Vanadyl acetylacetonate is the chemical compound with the formula VO(acac)2, where acac– is the conjugate base of acetylacetone. It is a blue-green solid that dissolves in polar organic solvents. The coordination complex consists of the vanadyl group, VO2+, bound to two acac– ligands via the two oxygen atoms on each. Like other charge-neutral acetylacetonate complexes, it is not soluble in water.

## Synthesis[edit]

The complex is generally prepared from vanadium(IV), e.g. vanadyl sulfate:[1]

VOSO4 \+ 2 Hacac → VO(acac)2 \+ H2SO4

It can also be prepared by a redox reaction starting with vanadium pentoxide. In this reaction, some acetylacetone is oxidized to 2,3,4-Pentanetrione.[1]

## Structure and properties[edit]

The complex has a square pyramidal structure with a short V=O bond. This d1 compound is paramagnetic. Its optical spectrum exhibits two transitions. It is a weak Lewis acid, forming adducts with pyridine and methylamine.[1]

## Applications[edit]

It is used in organic chemistry as a catalyst for the epoxidation of allylic alcohols by tert-butyl hydroperoxide (TBHP). The VO(acac)2–TBHP system exclusively epoxidizes geraniol at the allylic alcohol position, leaving the other alkene of geraniol untouched. By comparison, m-CPBA, another epoxidizing agent, reacts with both alkenes, creating the products in a two to one ratio favoring reaction at the alkene away from the hydroxyl group. TBHP oxidizes VO(acac)2 to a vanadium(V) species which coordinates the alcohol of the substrate and the hydroperoxide, directing the epoxidation to occur at the alkene close to this coordination site.[2][3]

## Biomedical aspects[edit]

Vanadyl acetylacetonate exhibits insulin mimetic properties, in that it can stimulate the phosphorylation of protein kinase B (PKB/Akt) and glycogen synthase kinase 3 (GSK-3).[4] It has also been shown inhibit tyrosine phosphatase (PTPase), PTPases[clarification needed] such as PTP1B, which dephosphorylates insulin receptor beta subunit, thus increasing its[clarification needed] phosphorylation, allowing for a prolonged activation of IRS-1, PKB, and GSK-3, allowing them to exert their anti-diabetic properties.[4]

## External links[edit]

* Oxidations tutorial

## References[edit]

1. ^ a b c Rowe, Richard A.; Jones, Mark M. (1957). "Vanadium(IV) Oxy(acetylacetonate)". Inorganic Syntheses. 5: 113–116. doi:10.1002/9780470132364.ch30. ISBN 978-0-470-13236-4.
2. ^ Itoh, Takashi; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Teranishi, Shiichiro (1979). "Vanadium-catalyzed epoxidation of cyclic allylic alcohols. Stereoselectivity and stereocontrol mechanism". Journal of the American Chemical Society. 101 (1): 159–169. doi:10.1021/ja00495a027.
3. ^ Rossiter, Bryant E.; Wu, Hsyueh-Liang; Hirao, Toshikazu (2007-03-15). "Vanadyl Bis(acetylacetonate)". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rv003m.pub2. ISBN 978-0471936237.
4. ^ a b Mehdi, Mohamad Z.; Srivastava, Ashok K. (2005). "Organo-vanadium compounds are potent activators of the protein kinase B signaling pathway and protein tyrosine phosphorylation: Mechanism of insulinomimesis". Archives of Biochemistry and Biophysics. 440 (2): 158–164. doi:10.1016/j.abb.2005.06.008. PMID 16055077.

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* t
* e

Vanadium compounds

Vanadium(0)|

* V(CO)6

Vanadium(II)|

* VBr2
* VCl2
* VI2
* VO
* VS

Vanadium(III)|

* VBr3
* VCl3
* VF3
* VI3
* VN
* V2O3
* V2(SO4)3
* V2S3

Vanadium(IV)|

* VC
* VO2
* VOCl2
* V(S2)2
* VCl4
* VF4

| Organovanadium(IV) compounds|

* VO(C5H7O2)2

|

Vanadyl(IV) compounds|

* VOSO4

Vanadium(V)|

* V2O5
* VOCl3
* VOF3
* VO2F
* VF5
* VCl5
* NH4VO3
* VOPO4

| Vanadyl(V) compounds|

* VO(ClO4)3
* VO(NO3)3

|

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Metal acetylacetonate complexes

| H(acac) |  |  |  | He

|
|
|
|

Li  | Be  | B  | C  | N  | O  | F  | Ne
Na(acac) | Mg  | Al(acac)3 | Si  | P  | S  | Cl  | Ar
K  | Ca  |  | Sc(acac)3 | Ti(acac)2Cl2
Ti(acac)3 | V(acac)3
VO(acac)2 | Cr(acac)2
Cr(acac)3 | Mn  | Fe(acac)2
Fe(acac)3 | Co(acac)2
Co(acac)3 | [Ni(acac)3]2 | Cu(acac)2 | Zn(acac)2 | Ga(acac)3 | Ge  | As  | Se  | Br  | Kr
Rb  | Sr  |  | Y(acac)3 | Zr(acac)4 | Nb  | MoO2(acac)2 | Tc  | Ru(acac)3 | Rh(acac)(CO)2
Rh(acac)3 | Pd(acac)2 | Ag  | Cd  | In(acac)3 | Sn  | Sb  | Te  | I  | Xe
Cs  | Ba(acac)2 | *  | Lu(acac)3 | Hf(acac)4 | Ta  | W  | Re  | Os  | Ir(acac)3 | Pt(acac)2 | Au  | Hg  | Tl(acac) | Pb  | Bi  | Po  | At  | Rn
Fr  | Ra  | **  | Lr  | Rf  | Db  | Sg  | Bh  | Hs  | Mt  | Ds  | Rg  | Cn  | Nh  | Fl  | Mc  | Lv  | Ts  | Og

*  | La(acac)3 | Ce(acac)3 | Pr(acac)3 | Nd(acac)3 | Pm  | Sm(acac)3 | Eu(fod)3
Eu(acac)3 | Gd(acac)3 | Tb(acac)3 | Dy(acac)3 | Ho(acac)3 | Er(acac)3 | Tm(acac)3 | Yb(acac)3
**  | Ac  | Th  | Pa  | U  | Np  | Pu  | Am  | Cm  | Bk  | Cf  | Es  | Fm  | Md  | No
*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
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