Structure and formation of the first (-O-Te-N-)4 ring

Area of Science:

• * Inorganic Chemistry
• * Organic Chemistry
• * Computational Chemistry

Background:

• * Macrocyclic compounds are of significant interest due to their diverse applications.
• * The synthesis of novel ring systems containing tellurium (Te) presents unique challenges and opportunities.
• * Understanding the formation mechanisms of complex organic molecules is crucial for synthetic advancements.

Purpose of the Study:

• * To synthesize a novel twelve-membered macrocycle incorporating a periodic -O-Te-N- sequence.
• * To elucidate the reaction pathway and mechanism for the formation of this macrocycle.
• * To investigate the structural and electronic properties of the synthesized compound using computational methods.

Main Methods:

• * Reaction of a β-(N,N-dimethylcarbamoyl-chalcogeno)-alkenyl ketone with hydroxylamine-O-sulfonic acid.
• * Characterization of the resulting macrocyclic product.
• * Density Functional Theory (DFT) calculations to model the reaction mechanism and intermediate structures.

Main Results:

• * Successful synthesis of a twelve-membered macrocycle with the characteristic -O-Te-N- sequence.
• * Identification of an intermediate isotellurazole-N-oxide species.
• * Computational analysis supported a mechanism involving spontaneous catenation of the intermediate.

Conclusions:

• * A novel synthetic route to a unique tellurium-containing macrocycle has been established.
• * The formation of the macrocycle proceeds via a spontaneous catenation of an isotellurazole-N-oxide intermediate.
• * This study expands the scope of macrocyclic chemistry and provides insights into tellurium-nitrogen-oxygen ring systems.