Module CCE 1102 Physical Theory

Data Sheet Experiment P7

Visualising the Structures of Common Analgesics

Parts 1 and 2
1. Copy or insert structures of a) salicylic acid (this has been done for you as an
example); b) acetyl salicylic acid; c) (R,S)-2-(4-isobutylphenyl)propanoic acid;
and d) N-(4-hydroxyphenyl)acetamide drawn in ChemDraw with the name of the
molecule typed below the structure in ChemDraw into the table below.

a) Salicylic Acid

Molecular Formula __C7H6O3____________

Average mass ____138.121_____________

Number of H-bond acceptors ___3________

Number of H-bond donors ___2__________

Log P ___2.06________________________

b) Acetyl Salicylic Acid

Commercial
Name______Aspirin_______________

Molecular Formula C9H8O4

Average mass __ 180.157

Number of H-bond acceptors ___4

Number of H-bond donors __1____

Log P _______________________________
 Module CCE 1102 Physical Theory

c) (R,S)-2-(4-isobutylphenyl)propanoic acid

Commercial
Name___________Ibuprofen___________

Molecular Formula C13H18O2

Average mass _ 206.281

Number of H-bond acceptors _2

Number of H-bond donors _1

d) N-(4-hydroxyphenyl)acetamide

Commercial
Name___________Paracetamol___________

Molecular Formula C8H9NO2

Average mass 151.163

Number of H-bond acceptors _3_____

Number of H-bond donors _2___

[30 MARKS]
2. List these compounds in order of hydrophobicity. Explain how this order was
determined and using the structure of the molecules suggest an explanation for this
order.
[20 MARKS]
 Module CCE 1102 Physical Theory

Part 3
1. Show the optimised structures of a) salicylic acid (given as an example); b) acetyl
salicylic acid; c) (R)-2-(4-isobutylphenyl)propanoic acid; and
d) N-(4-hydroxyphenyl)acetamide obtained using Chem 3D.

a) salicylic acid b) acetyl salicylic acid

Final Energy: Final Energy: 9.4152 kcal/mol

c) (R)-2-(4-isobutylphenyl)propanoic acid d) N-(4-hydroxyphenyl)acetamide

Final Energy: Final Energy:

[15 MARKS]
 Module CCE 1102 Physical Theory

2. Show the optimised structures of a) salicylic acid (given as an example); b) acetyl

salicylic acid (aspirin) with the intramolecular hydrogen bond.

a) salicylic acid – phenol as H-bond b) acetyl salicylic acid

donor and hydroxy acceptor

c) salicylic acid – phenol as H-bond

donor and carbonyl acceptor

[10 MARKS]
3. Suggest how the presence of an intramolecular H-bond could influence the solubility
of these compounds in water and their interaction with the COX enzyme.

Intramolecular H-bonding would decrease the solubility of the compound and it would
require a higher temperature dissolution. This is because the hydrogen molecules
are not in the best orientation for hydrogen bonding between the compound and
water molecules to occur. The polar H bonds are involved in intramolecular
interactions and are then unavailable to form intermolecular H bonds with solvent
water molecules. Additionally, the molecule would have less interaction with the COX
enzyme as there are less docking sites available due to hydrogen atoms being
involved in intramolecular interactions.
 Module CCE 1102 Physical Theory

[10 MARKS]
4. Show a screen shot of aspirin and the COX enzyme obtained in mcule.
[15 MARKS]