Intra- and intermolecular hydrogen bonding in solutions of N-(2-hydroxy-3,8-diiodocyclooctyl)trifluoroacetamide and N-(4-iodo-2,2,5,5-tetramethyltetrahydrofuran-3-yl)trifluoroacetamide


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Abstract

The methods of IR spectroscopy and quantum chemistry (B3LYP/DGDZVP) were applied to investigation of the types of self-associates formed in solutions of N-(2-hydroxy-3,8-diiodocyclooctyl)trifluoroacetamide and N-(4-iodo-2,2,5,5-tetramethyltetrahydrofuran-3-yl)trifluoroacetamide in CCl4 by means of hydrogen bonding. The ОН group of N-(2-hydroxy-3,8-diiodocyclooctyl)trifluoroacetamide participates in the formation of intramolecular hydrogen bond ОH···О=С, while chain dimers are formed due to interactions between the NH and С=О groups of the neighboring molecules. Due to the formation of the intramolecular bond, the dimers of N-(2-hydroxy-3,8-diiodocyclooctyl)trifluoroacetamide are energetically less stable than the chain dimer of N-(4-iodo-2,2,5,5-tetramethyltetrahydrofuran-3-yl)trifluoroacetamide.

About the authors

I. V. Sterkhova

A.E. Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: bagrat@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

V. V. Astakhova

A.E. Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: bagrat@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

B. А. Shainyan

A.E. Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Author for correspondence.
Email: bagrat@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

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