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Student Name
BHEBE NKWANELE
B1441641
. Course Code: CH202
Reg. No.
NdlovuSilibaziso
B1441653
B1441603
B1441751
AIM(S)
To synthesise a (VO)2+ Complex ( acetylacetonate complex,)
OBJEVTIVE(S)
To investigate cytotoxic activities of VO2+ complexes against human
cancer cells,by studying literature of VO2+ complexes
To prepare vanadium acetoacetonate by deprotonating a mixture of
tautomer keto and enol to form acetylacetonate anion (acac)
To encourage even boiling,by using boiling chips placed in the flask
with the mixture during refluxing
To observe, record and interpret empirical observations
To calculate the % yield of [VO(acac)2]
Introduction
Oxovanadium complexes exhibit cytotoxic activities against human cancer
cell lines. These chemicals are able to kill target cancer cells at low
micromolar concentrations [1]. Current literature suggests that the therapeutic
characteristics of these metal complexes are influenced by the identity of the
five membered bidentate ligands, as well as the nature of the substituents
on the heterocyclic ring.
Acetyl acetone (2, 4-pentanedione) is a -dike tone. The carbon atom of the
CH2 group in between the 2 carbonyl group is -carbon and the hydrogens
attached to it are acidic. This is due to the presence of 2 electron
withdrawing carbonyl groups. The -hydrogen may be easily lost to water to
produce an anion stabilised by resonance.
The acetylacetonate anion can then act as a ligand towards the oxovanadium
cation to produce VO (acac) 2. This ligand bonds to the metal ion through
both its oxygen atoms and, hence, a six membered, weakly aromatic ring is
produced.
APPARATUS/EQUIPMENT
round-bottom flask, 250ml conical flask, 500 ml conical flask,
concentrated H2SO4 , of ethanol, vanadium pentoxide, V2O5 , hydrated
Na2CO3
Procedure
10.0 ml of distilled water was added to a 50 ml round-bottom flask, followed
by the careful addition of an equal volume of concentrated H2SO4.
Then, 25.0 ml of ethanol and 5 g of vanadium pentoxide, V2O5, was added to
the round-bottom flask. The flask was thereafter connected a water cooled
vertical condenser and refluxed vigorously in a heating mantle at a setting of
10 for an hour. The mixture was swirled every 5 minutes. The orange V2O5
solid dissolves in the colourless solvent to produce a dark blue-green
solution.
After an hour, the mixture was cooled in water and filtered using vacuum
filtration. The solid residue was discarded. The filtrate was poured into a
250ml conical flask. 13 ml of acetylacetone was added drop wise to the
filtrate with shaking. The mixture was then neutralised by adding it carefully
to a solution of 20 g of hydrated Na2CO3 in 125 ml deionised water, contained
in a 500 ml conical flask, while swirling the flask.
The resulting mixture was cooled in an ice water bath, before it was filtered
at the pump. The dark green product was washed with cold deionised water
and thereafter, sucked dry by the vacuum pump. The dried product was then
weighed and the percentage yield, determined.
Results and calculation
Empirical observations
Preparation of VO (acac) 2
2.00 g
1
37,013
39,013
2
37,013
39,013
3
37,013
39,013
2,00
2,00
2,00
1
37,013
57,013
2
37,013
57,013
3
37,013
57,013
20,00
20,00
20,00
1
1,0561
2
1,0561
3
1,0561
5,4661
5,4661
5,4661
4.41
4,41
4,41
4,41g
Mass of product=4,41g
Mass of filter
paper/g
Mass of paper +
product/g
Mass of product/g
V2O5 + 4H+
(VO)2+ + 2 acacH
2H+ + VO (acac)2
(1)
(2)
Spectrum obtained,
VO(acac)2py
V=O
stretching
965.3 cm-1
Sample spectrum, VO
(acac)2
997 cm-1
VO(acac)2. More time is required to leave the mixture to stand in an ice bath
for crystallisation after Na2CO3 is added in order to produce a higher yield of
VO(acac)2. More base may be added to favour the formation of the desired
product as well.
Precautions
As the reagents may be toxic, gloves were worn to protect the hands. This is
especially important when handling corrosive reagents such as concentrated
sulphuric acid. The experiment was carried out in the fumehood to prevent
any inhalation of harmful organic vapours. The flammable reagents
acetylacetone) were also placed away from naked flames.
Also, the solution of (VO)2+ was not filtered with cotton wool, which was
suggested by the lab schedule. Instead, filter papers were used. This was
because cotton wool may be easily dislodged and thus, allow unreacted V 2O5
to pass through. By contrast, filter paper is more effective at separating the
insoluble unreacted reagent and soluble product[4] .
Conclusion
The preparation and chemical analysis of oxovanadium acetylacetonate,
allow the chemical properties of the product to be characterised. The
percentage yield of VO(acac)2.
(i)
The formula of the product is VO ( acac)2. Name and draw the structure of
the Complex.
(VO)2+ + 2CH3COCH2COCH3
2 H+ + VO(CH3COCHCOCH3)2
C10H16O5V Vanadium(V)-oxyacetylacetonate
Structure of the complex
(ii)
Record the yield and calculate the percentage yield of the reaction.
Percentage yield of VO (acac)2 = 4.41 / 5.831 x 100% 75.6 %
(iii)
How would you expect the compound to react with pyridine? Give the
structure
Of the expected product.
Pyridine has a lone pair of electrons on the N atom which can be used to bind
with the central vanadium ion to form a 6-coordinated complex. The overall
structure of the grey complex, VO(acac)2py, will be octahedral
VO(acac)2 + py
VO(acac)2py
References