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

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 iodocycli...

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Bibliographic Details
Published in:Journal of molecular structure 2016-09, Vol.1119, p.227-234
Main Authors: Matveychuk, Y.V., Ilkaeva, М.V., Vershinina, E.A., Batalov, V.I., Morozov, R.S., Bartashevich, E.V.
Format: Article
Language:English
Subjects:
Alkenylthioquinolines
Chemical bonds
Electronic absorption spectra
Halogens
Iodine halogen bonds
Mathematical models
Modelling
Molecular structure
Process control
Spectra
Spectroscopy
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Summary: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. [Display omitted] •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.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2016.04.072