Synthesis and Characterization of Schiff

base ligands and their application in the

Formation of coordination compounds
By
Shakir nabi
Registration no.11918754
Bsc(Hons) chemistry
Lovely Professional University ,Phagwara
Punjab ,India
Introduction
•Schiff bases, also known as Imines or Azomethine

•Hugo Schiff was a chemist who discovered a chemical with the

general structure R1C=NR'(R≠H) .

•Schiff bases are a type of base with the general formula R'R"C=NR"'

that are made primarily by condensation of an aldehyde or ketone

with a primary amine (as aniline) .

•Used as intermediates in organic synthesis and can also act as

dyes.
 Synthesis of Schiff Bases

A common method of synthesis of Schiff base is the nucleophilic

attack of amines on electrophilic carbon of aldehydes or ketones.

The end result of this reaction is a compound in which C=O double

bond is replaced by a C=N double bond .This type of compound is

called an imine or a Schiff base.

 Mechanism

•The mechanism of Schiff base formation involves two major steps .

First is the attack of the amine nitrogen on the carbonyl carbon. The

nitrogen is deprotonated and the electrons from this N-H bond

then push the oxygen off the carbon, forming a C=N double bond

and displace water molecules.

 Some other methods of synthesis of Schiffs base

•Other methods of preparation of Schiff base are by Oxidative

synthesis of imines from alcohols and amines, oxidative

synthesis of imines from amines, addition of organo-metallic

reagents to cyanides, reaction of phenols and phenol-ethers

with nitriles, oxidation of metal amines to imines by 2-

Bromo-anisole and Conversion of α-amino acids into imines.

 Coordination compounds

•coordination compound is any of the grades of substances that are

composed of chemical structures in which a central metal atom is

surrounded by non-metal atoms or groups of atoms, called ligands.

Ligands

•A ligand is an ion or molecule, which donates a pair of electrons

to the central metal atom or ion to form a coordination complex.

 Types of ligands

•Mono dentate Ligands

Monodentate ligands are also called “one-toothed“ because they bite
the metal atom only in one place.E.g Br ,Cl ,Co ,OH etc.
•Bidentate Ligands
Lewis base which donates two lone pairs of electrons to the central
metal atom is known as bidentate ligands. They are often referred to
as a “chelating ligands”. E.g Ethylenediammine (en) , Acetylacetonate
ion (acac) etc.
•Tridentate Ligands and Polydentate Ligands
Tridentate ligands have three lone pairs of electrons to the central
metal atom or ion. Molecules with four donor atoms are called
tetradentate, five donor atoms are called pentadentate and six donor
atoms are called hexadentate. They are generally mentioned as
polydentate ligands. E,g
Diethylenetriamine(tridentate) ,Triethylenetetraamine(tetradentate)
 Complex formation of Schiffs base

•Schiff base have been used as chelating ligands in coordination

chemistry and metal complexes of these ligands attracted great
interest.

•Chelating ligands containing N, O and O donor atoms show broad

biological activity. These are of special interest because of the special
way they are bonded to the metal ions.

•Metal complexes of Schiff base find applications in various fields:

the most prominent is in the field of catalysis.

•Aromatic Schiff base or their metal complexes catalyse reactions on

oxygenation, hydrolysis, electro-reduction and decomposition.
 Applications

Anticancer properties:

Schiff base has anticancer effects and can be used to blood

disorders because it can disrupt the enzyme Ribonucleotide

Reductase.

Biological activity:

Their biological properties have an antifungal and antibacterial

effect. In biological sciences, the amino group aids the

mechanism of racemisation reaction

Application in modern technologies:

Its biological, photo chromic, and thermo chromic qualities make it

suitable for usage in today's technologies. It can be used to measure

and control radiation intensity. Modern optical computers and photo

detectors also employ it. Because the aromatic ring contains an electron

cloud and an electronegative element .In steel, aluminium, copper, and

moderate or acidic environments , it works as an anticorrosive.

Anti-malarial qualities include the following:

Malaria is a dangerous disease that can have major and

harmful consequences for our bodies. It is caused primarily by

plasmodium species. Ancistro cladidine, for example, is an

antimalerial schiff base.

Manufacturing and chemical preparations applications include:

Schiff bases are the primary messengers in reactions involving

polycyclic and isoquinoline derivatives. These chemicals are

used to make Ruhemann's purple, a reaction between ninhydrin and

amino acids that is used to discover fingerprints .