Chapter 14: Problem 66
Toradol is used in dentistry to relieve pain. Name the functional groups in
this molecule.
Short Answer
Expert verified
Toradol has benzene rings, carbonyl groups, a carboxylic acid group, and a nitrogen-containing ring.
Step by step solution
01
- Identify the molecule structure
The SMILES notation for Toradol is given. Convert this notation into its corresponding molecule structure.
02
- Identify the aromatic rings
Find the benzene ring in the structure, which is identified by 'c1ccccc1', and the fused bicyclic ring, 'c1ccc2n1CCC2'. Aromatic rings generally represent stability and delocalized electrons.
03
- Identify the carbonyl groups
Locate the carbonyl groups, represented by 'O=C'. In this molecule, there are two carbonyl groups: one attached to the benzene ring and one forming a part of the carboxylic acid group.
04
- Identify the carboxylic acid group
A carboxylic acid group is represented by 'C(=O)O'. Find this group in the molecule, typically composing a carbonyl group directly bonded to a hydroxyl group.
05
- Identify the nitrogen-containing ring
Identify the nitrogen atom within the bicyclic ring system, 'c1ccc2n1CCC2'. The nitrogen atom forms part of a heterocyclic structure.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
SMILES notation
The SMILES (Simplified Molecular Input Line Entry System) notation is a way to represent a chemical structure using a string of characters. It allows for the easy sharing of molecular information in a compact format. In the case of Toradol, the SMILES notation is O=C(c1ccccc1)c1ccc2n1CCC2C(=O)O . Each character or set of characters in this string represents a specific part of the molecule:
- 'O' and 'C' represent oxygen and carbon atoms, respectively
- '=' denotes a double bond
- 'c1ccccc1' signifies a benzene ring, an aromatic system
- 'c1ccc2n1CCC2' represents a fused bicyclic ring with a nitrogen atom (a heterocycle)
Aromatic rings
Aromatic rings are cyclic structures with alternating double and single bonds, allowing for a stable, resonant bonding system. In Toradol, the benzene ring is characterized in the SMILES notation by 'c1ccccc1'. Aromatic rings exhibit unique properties, such as:
- High stability due to delocalized electrons
- Special reactivity patterns in chemical reactions
- Distinctive spectroscopic signatures used in identification
Carbonyl groups
Carbonyl groups are functional groups characterized by a carbon atom double-bonded to an oxygen atom (C=O). Toradol contains two carbonyl groups:
- One attached to the benzene ring, denoted in the SMILES by 'O=C(c1ccccc1)'
- Another as part of the carboxylic acid group, shown in the SMILES as 'C(=O)O'
Carboxylic acid group
A carboxylic acid group consists of a carbonyl group (C=O) directly bonded to a hydroxyl group (OH), represented commonly as COOH in chemical structures. In the SMILES notation for Toradol, the carboxylic acid group is indicated by 'C(=O)O'. Characteristics of carboxylic acids include:
- Acidic properties due to the ability to donate a proton (H+)
- Solubility in water and polar solvents
- Reactiveness in forming esters, amides, and other derivatives
Heterocyclic structures
Heterocyclic structures are rings that contain at least one atom other than carbon, often leading to unique chemical properties. In Toradol, the heterocyclic structure includes a nitrogen atom in the fused bicyclic ring, represented by 'c1ccc2n1CCC2' in its SMILES notation. Heterocycles are significant in pharmaceuticals due to:
- Diverse structural variations and functionalities
- Enhanced pharmacological activity and specificity
- Key roles in the design of drugs and bioactive compounds