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where atoms N1, N2, N4, C, S lie in the same plane, two atoms S and N1
are at trans-position each other.
Because of containing group NH2, thiosemicarbazide easily reacts with
carbonyl compounds to form thiosemicarbazone. This is condensation
reaction where atom N1 plays the role as nucleophile, atom C of carbonyl
group is electrophile center. Catalyst of reaction is acid.
Mechanism of reaction:
R H
R
δ+ δ- ..
C O + H2N NH C NHR'' R' C N
+
NH C NHR''
R'
S O- H S
R R
H2N S S NH2 HS NH S
NH2
Figure 2: Forming complex of thiosemicarbazone diagram
R1 O
NH NH2
HN N N NH
H2N
+ 2
S S + 2 H2O
S
R2 O NH2 H2N
Ph Ph Ph Ph
N N N N
N N HN NH
Pd Cu
H2N NH2
S S S NH HN S
H3C CH3
N
N N
HN NH
S NH2 H2N S
CH3 N
HN NH2
O N
H
S (TB1)