Difference Between Imidazole and Triazole

The key difference between imidazole and triazole is that imidazole has non-adjacent nitrogen atoms in its chemical structure whereas triazole has adjacent nitrogen atoms in its chemical structure.

Both these compounds are important medicines and have many other applications as well. Some chemical facts about these two compounds are discussed below in this article.

CONTENTS

1. Overview and Key Difference
2. What is Imidazole
3. What is Triazole
4. Similarities Between Imidazole and Triazole
5. Side by Side Comparison – Imidazole vs Triazole in Tabular Form
6. Summary

What is Imidazole?

Imidazole is an organic compound having the chemical formula C₃N₂H₄. At room temperature, it is a solid with a white to pale yellow color. This compound is highly soluble in water; it forms an alkaline solution. When considering its chemical structure, it has a heterocyclic ring made of both carbon and nitrogen atoms. And thus, it is an aromatic structure. Also, it falls into the category of diazoles due to the presence of two nitrogen atoms and three carbon atoms in its ring structure.

Some important chemical facts about imidazole are as follows:

• Chemical formula = C₃N₂H₄
• Molar mass = 68.077 g/mol
• Appearance = white to pale yellow solid
• Crystal structure = monoclinic
• Melting point = 90.5 °C
• Boiling point = 257 °C

Figure 1: Tautomerism in Imidazole

Further, Imidazole is a planar structure and has two tautomers (constitutional isomers). Moreover, this compound is highly soluble in water due to its polarity. The electric dipole moment of it is around 3.67 Debye. More importantly,  it is amphoteric, meaning this compound can act as both acid and base.

What is Triazole?

Triazole is an organic molecule having the chemical formula C₂H₃N₃ and molar mass 69.07 g/_mol.. This compound has a five-membered ring containing three nitrogen atoms and two carbon atoms. Unlike imidazole, triazole has adjacent nitrogen atoms. Furthermore, it has different forms of isomers; these molecules fall into different groups based on the location of the N-H bond. Moreover, these molecules show tautomerism.

Figure 2: Chemical Structure of 1H-1,2,3-Triazole

Triazole is useful in making antifungal drugs such as fluconazole, voriconazole, etc. Further, it is useful as a fungicide for plant protection. Some compounds that contain triazole are useful as plant growth retardants (plant growth regulators).

What are the Similarities Between Imidazole and Triazole?

• Imidazole and Triazole are organic compounds.
• Both have five-membered ring structures.
• Further, they show Tautomerism.
• Also, both compounds have N-H bonds.

What is the Difference Between Imidazole and Triazole?

Summary – Imidazole vs Triazole

Imidazole and triazole are important cyclic structures used to produce different medicine and compounds used in agriculture. Overall, the key difference between imidazole and triazole is that imidazole has non-adjacent nitrogen atoms in its chemical structure whereas triazole has adjacent nitrogen atoms in its chemical structure.

Reference:

1. “Imidazole.” Wikipedia, Wikimedia Foundation, 30 Apr. 2018, Available here.
2. “Imidazole.” National Center for Biotechnology Information. PubChem Compound Database, U.S. National Library of Medicine, Available here.
3. “Triazole.” Wikipedia, Wikimedia Foundation, 27 Apr. 2018, Available here.

Image Courtesy:

1. “Resonance-imidazole” By Mrgreen71 – Own work (CC BY-SA 3.0) via Commons Wikimedia
2. “1H-1,2,3-Triazole Structural FormulaV” By Jü – Own work (CC BY-SA 3.0) via Commons Wikimedia

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