Arylpentazoles with surprisingly high kinetic stability

Area of Science:

• Organic Chemistry
• Chemical Kinetics
• Computational Chemistry

Background:

• Arylpentazoles, known for over a century, possess inherent kinetic instability.
• Their application is limited to in situ generation of the pentazole anion due to poor stability.

Purpose of the Study:

• To enhance the kinetic stability of arylpentazoles.
• To enable broader applications of arylpentazoles by overcoming stability limitations.

Main Methods:

• A novel co-stabilization strategy was proposed and investigated.
• Computational chemistry methods, specifically the CBS-QB3 level, were employed for theoretical calculations.

Main Results:

• The N2-leaving barrier of arylpentazoles was significantly increased.
• The highest recorded N2-leaving barrier reached 40.83 kcal mol-1.
• The co-stabilization method proved effective in enhancing kinetic stability.

Conclusions:

• The developed co-stabilization method successfully enhances arylpentazole kinetic stability.
• This advancement makes arylpentazoles more amenable to broader chemical applications.
• The findings pave the way for utilizing arylpentazoles beyond in situ generation.