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Carbene

Carbene is an electron deficient species containing a divalent carbon atom with two unshared valence electrons. There are two main types of carbenes: singlet carbenes which have no unpaired electrons and triplet carbenes which have one pair of unpaired electrons. Triplet carbenes are more stable due to electron repulsion in the singlet state. Carbenes are further classified as heteronuclear or homonuclear transition metal carbene complexes. Heteronuclear complexes contain carbene carbons bonded to electronegative heteroatoms, while homonuclear complexes have alkyl or hydrogen groups bonded to the carbene carbon.

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687 views7 pages

Carbene

Carbene is an electron deficient species containing a divalent carbon atom with two unshared valence electrons. There are two main types of carbenes: singlet carbenes which have no unpaired electrons and triplet carbenes which have one pair of unpaired electrons. Triplet carbenes are more stable due to electron repulsion in the singlet state. Carbenes are further classified as heteronuclear or homonuclear transition metal carbene complexes. Heteronuclear complexes contain carbene carbons bonded to electronegative heteroatoms, while homonuclear complexes have alkyl or hydrogen groups bonded to the carbene carbon.

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Harman Preet Kaur
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Carbenes

1 Carbene
Types and
2
stability
3 Classification
Content
Add your text
Carbene is a molecule containing a neutral carbon
atom with a valence of two and two unshared valence
electrons.
 Uncharged species
 Electron deficient
species that  having two non -
bonded electrons on
contain divalent Carbene carbon atom
atom surrounded
Or
by sextet of
electron and two Carbenoid  Types :
susbtituents • Singlet carbene
 Eg. :CH2 , :CX2 • Triplet carbene
X= Halogen ( F , Cl , Br )
Singlet carbene Triplet carbene
1. Carbene group that
has no unpaired
electrons.
2. It has bent geometry.
3. It is diamagnetic
4. It has sp² hybrid structure.
5. Has electrophilic and 5. It has radical or diradical type
nucleophilic behaviour. behaviour.
6. Less stable and higly reactive. 6. It is more stable and less reactive.
7. S= 2s+1= 2*(-1/2+1/2)+1= 1 7. S= 2s+1= 2*(1/2+1/2)+1= 3
8. It violates hundꞋs rule 8. It follows hund's rule
9. Prefer Stereospecific reaction. 9. Non stereospecific
10. Mainly occur in aqueous 10. Occurs in gaseous state.
medium
Triplet vs. Singlet
P
S
↑↓ Sigma
~8-10 Kcal mol-1
T ↑ ↑
P Sigma

Triplet carbene is more stable than singlet carbene because of presence of 8-10kcal mol-1 lower
in energy than the singlet carbene. The triplet carbene is present in ground state which is more
stable state than excited state and due to repulsion in singlet state there is energy required to
pair the electrons called pairing energy in sigma orbital.
If the small energy difference between the sigma and p orbital then the electrons remain
unpaired i.e. triplet state.
If a large gap between the sigma and p orbital the electrons will pair in the sigma orbital
i.e. singlet state.
Classification of carbene :
The transition metal-carbene complexes are of two types:
[A] Heteronuclear carbene complexes:
The carbene complexes of general type LnM[:C(R)RꞋ]
Where either R or RꞋ or both electronegative heteroatoms bonded to carbene carbon
having lone pair . Eg. halogen, :NH2 , :NMe2 etc.
These carbenes are also known as Fischer Carbenes because the first complex
was discovered by E.O.Fischer and A. Mossbol in 1964.The first complex of this
category was [CO5W=C(OCH3)Ph]
[B] Homonuclear carbene complexes:
The carbene complexes of the general type [Ln M[:C(R)RꞋ]
Where both R and RꞋ either hydrogen atom or alkyl groups .
These carbenes are also known as
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Schrock Carbenes becauseAdd
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the ityour
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first
discovered by R.R.Schrock in 1974.
here,according to
The complex discovered by here,according
h er e ,a c c or d i n g t o
schrock of thisto
category was [(Cp)2(CH3)Ta=CH2your
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Where Cp= Cyclopentadienyl
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Fischer carbene R Schrock carbene
LnM=C
RꞋ
1. C=6 1s2 ,2s2, 2p2 1. C=6 1S2 , 2S2 , 2P2
G.S. ↑↓ ↑ ↑ 01 G.S. ↑↓ ↑ ↑

sp2 hybridisation A d d y o u r title E.S. ↑ ↑ ↑ ↑


R or RꞋ= :NR2,:O:Me2 sp hybridisation
2. (CO)5Cr=C NMe2 H
2. (Cp)2Ta=C R or RꞋ=
Me M=MO(0),W(0),Cr(0) CH3 M=Ta(5),W(6)
Me,H
L= CO,PR3 L=Cl,Cp
3. The carbene carbon is electrophilic
A d d y o uin
r nature
title
3. Carbene carbon is nucleophilic.
4. The R or RꞋare pi donor heteroatoms.
4. The R orRꞋ are not pi donors.
5. Ligands (L) are good pi acceptor.
02
6.Metals present in low oxidation state i.e. 0
5.ligands are non pi acceptor.
6.Metals are in high oxidation state.
7.These are formed by singlet carbenes
7.These are formed by triplet
which behave as 2e- lone pair donor ligand.
carbenes.
8.It mostly obeys 18e- rule.
8.It mostly doesnot obey 18e- rule.

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