Allyl vs ethyl substituted thioquinoline complexes with diiodine: Halogen bonds and iodocyclization

• Bands related to iodine halogen bonds are disguised by iodocyclization products.
• 2-allylthioquinoline S-complexes with iodine have absorption about 290 and 370 nm.
• TD-DFT calculations for iodine complexes are in good agreement with UV/Vis spectra.
• UV/Vis spectra allow to control the staging of iodocyclization process.

A comparative analysis of 2-allylthioquinoline and 2-ethylthioquinoline interactions with diiodine in solutions was performed using UV/Vis spectroscopy and molecular modelling with a TD-DFT approach. The named compounds exhibit different reactivity: 2-allylthioquinoline participates in the iodocyclization reaction and 2-ethylthioquinoline forms molecular complexes with diiodine only. The emergences of iodocyclization products and diiodine complexes of alkyl- and alkeny lsubstituted thioquinolines on spectra allow us to enable process control of interactions with diiodine.

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