AROMATICITY
AROMATICITY
AROMATICITY
The term aromatic was originated from the word ‘aroma’ means
characteristic odour.
Cyclopropene
Cyclic, planar, 2 Pi electrons (n=0); delocalization due to SP3 methylene carbon
Nonaromatic
Cyclopropenyl cation
Cyclic, planar, 2 Pi electrons (n=0); delocalization is possible through the empty
'P'orbital
Aromatic
Cyclopropenyl anion
4 electron (even number of pairs; 4n, n=1)
Antiaromatic; not stable
Four membered ring compounds
Cyclobutadiene
Cyclobutadienyl dication
Cyclic, planar, continuous delocalization of Pi electrons, posses (4n+2) Pi electrons
Aromatic
Cyclopentadiene
Cyclic, planar, posses 4n Pi electrons, delocalization of electrons interrupted
by SP3 hybridized carbon
Non aromatic
Cyclopentadienyl cation
Cyclic, planar, continuous delocalization of electrons, posses 4n Pi electrons
Antiaromatic
Cyclopentadienyl anion
Cyclic, planar, continuous delocalization of electrons, posses (4n+2) Pi
electrons
Aromatic
Seven membered ring compounds
Cycloheptatriene
Cyclic, planar, posses (4n+2) Pi electrons, no continuous
delocalization Pi electrons possible
Nonaromatic
Cycloheptatrienyl cation
Cyclic, planar, posses (4n+2) Pi electrons, continuous delocalization
Pi electrons possible
Aromatic
Cycloheptatrienyl anion
Cyclic, planar, posses (4n) Pi electrons, continuous delocalization Pi
electrons possible
Antiaromatic
Eight membered ring compounds
[12]- annulene
Aromatic
14 annulene
[16] annulene is nonplanar and shows signif icant bond alteration like polyene,
nonaroamtic in nature. Its dianion shows aromatic character
16 annulene
[18] annulene is planar, cavity is suf f iciently large and hence shows less
steric interactions of internal hydrogens. It shows continuous delocalization
of (4n+2) pi electrons and aromatic nature.
18 annulene
Homoaromaticity
H H
H
H
Aromaticity in fused rings
The criterion used for the monocyclic hydrocarbon can also be applied
for the polycyclic hydrocarbons. The resonance energy per pi electron
decreases with increase in aromatic ring. Larger polynuclear
hydrocarbons have a tendency to undergo addition reaction. Example is
Diel’s Alder reaction
H Br
Br2
H Br