Thiophine

Thiophene is a five membered heterocyclic compound

with formula C4H4S

First of all synthesized by Victor Meyer

400oC
2 HC CH + H2S
+ H2
Al2O3
S
(2) By high temperature reaction of sulfur with butane

H2 H2 600oC
H3C C C CH3 + 4S + 3H2S
S
(3) By heating sodium succinate with phosphorous trisulfide

H2C C ONa P2S3

H2C C ONa S

O
 Physical Properties

Colourless liquid, Odour similar to benzene

Boiling Point 84oC
Insoluble in water soluble in ethanol, ether and
acetone
Thipohene is much reactive than benzene
Thiophine Resonance forms
All ring atoms are SP2 hybridized
SP2 orbital's overlap with each other and
with S atomic orbital of hydrogen forming
sigma bond

C-C , C-S, C-H are the three types of sigma

bond
All sigma bond lie in one plane

The third SP2 orbital on sulfur is completely

filled
The pair of electron in this orbital account
for
one of the sulfur lone pair
Each ring atom has an unhybridized p
orbital and these are perpendicular to the
plane of sigma bond
P orbital on carbon contains one electron
each and p orbital on sulfur contains
two electron
The lateral overlap of these produces a
molecular orbital containing six electron
Thiophene shows aromaticity because
the
resulting molecular orbital satisfies the
Huckel rule
(i.e n=1 in 4n+2)
CHEMICAL PROPERTIES
 Thiophine undergoes electrophilic
substitution reaction at position number 2.
These reactions are nitration, sulphonation,
halogenation and acetylation
 Thiophine is less reactive towards
electrophilic substitution reaction as
compared to pyrrole