AROMATICITY (30seconds)

Thiazole is a 5 membered ring which consists of 3 Carbon, 1 nitrogen and 1 sulphur. All
of this are sp2 hybridized. Since it is sp2 hybridization, it makes thiazole as a planar
thiazole ring structure. Each ring atom has unhybridized p orbital that is perpendicular to
the plane of the sigma bond. The total number of non- bonding electrons are 6 which is 3
comes from the carbon, 1 from nitrogen and 2 from sulfur. The resonance of 6 electrons
shows thiazole follows the Huckels rule which is 4n+2 where n equals to 1. So, we can
conclude thiazole is an aromatic compound.

Reactivity(30s)
In thiazole, it undergoes nucleophilic substitution reaction at C2. It attacks at c2 bcs of
the electron deficient nature. In order to make the nucleophilic substitution occur, a
strong nucleophile or activation of the ring are needed. This reaction is more preferred at
c2 because position 2 is freely undergo substitution while c4 will not give any
substitution product and c5 does not give product as easily as at c2. So this is why
nucleophilic substitution reaction for thiazole attacks at c2.

30s
One of the drugs that contains thiazole is sulphathiazole. It is a short acting sulfonamide
antibiotic and used in combination of sulfabenzamide and sulfacetamide to treat vaginal
infections. It is effective against gram positive and gram negative pathogenic
microorganism.Although no longer used in humans, it is used in cattle.
The second drug is famotidine. It is a histamine H2 receptor antagonist that decreases the
stomach acid production. It is used to prevent ulcers in the stomach and intestines.
Another drug is thiamine or also known as vitamin B1. It is to prevent vitamin B1 deficiency. The
key features are

1m
For the proton nmr spectrum of thiazole, there are 3 types of protons where first proton is at C
bond to S and N, second types of proton at C bond to nitrogen and third type of proton is at
carbon attach to sulphur. This means there are 3 different signals of NMR spectrum that leads to
3 peaks. From the graph, this line shows A, the middle line is B and this line is C. In A, it is far
away from 0. It is downfield with highest ppm compared to the other 2 signals. This is bcs the
position of proton is near to the electronegative atom which is S and N. This causes the nucleus
proton to be deshielded. For the middle line, it is downfield too but has lower ppm compared to
A because the proton is attach only to nitrogen. It has also decreased shielding. For the most
right line which is shown as C, it has the lowest frequency compared to the other 2 signals
because it is attach to sulphur which is less electronegative than nitrogen. There is only one
proton gives the peak in line A,B and C which is 1H. For splitting, A is singlet as it does not have
any neighboring atom ,meanwhile for B and C it is doublet as they have one neighboring atom.

Next is about the mass spectrometry. The molecular ion peak is 85. In the first elimination, CHN
is eliminated. It is M-27. For the second elimination, CHCHN will be eliminated and causes it to
be M-40. Molecular peak or also known as base peak have 100%abundance.