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
- Authors: Sterkhova I.V.1, Astakhova V.V.1, Shainyan B.А.1
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Affiliations:
- A.E. Favorskii Irkutsk Institute of Chemistry, Siberian Branch
- Issue: Vol 87, No 8 (2017)
- Pages: 1680-1684
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/220945
- DOI: https://doi.org/10.1134/S1070363217080060
- ID: 220945
Cite item
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