Conformational Analysis and Study of Hydrogen Bonding of Iodobicycloheptanyl-N′-(trifluoromethanesulfonyl) Acetimidamides

Structure of iodobicycloheptanyl- N ′-(trifluoromethanesulfonyl) acetimidamide epimers and its self-associates in crystal, solution and gas phase was studied by X-ray diffraction, IR spectroscopy and quantum chemistry methods. In an isolated molecule, the 2 S ,7 R -enantiomer is energetically prefer...

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Bibliographic Details
Published in:Russian journal of general chemistry 2021-05, Vol.91 (5), p.807-813
Main Authors: Sterkhova, I. V., Fedorova, T. E., Moskalik, M. Yu
Format: Article
Language:English
Subjects:
Analysis
Bonding strength
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Conformational analysis
Crystal structure
Dimers
Enantiomers
Free energy
Heat of formation
Hydrogen
Hydrogen bonding
Hydrogen bonds
Infrared spectroscopy
Quantum chemistry
Sulfonamides
Vapor phases
X-ray diffraction
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Summary:Structure of iodobicycloheptanyl- N ′-(trifluoromethanesulfonyl) acetimidamide epimers and its self-associates in crystal, solution and gas phase was studied by X-ray diffraction, IR spectroscopy and quantum chemistry methods. In an isolated molecule, the 2 S ,7 R -enantiomer is energetically preferred, the structure of which is also realized in the crystal. According to X-ray diffraction analysis, in the crystal, (2 S ,7 R )- N -(7-iodobicyclo[2.2.1]heptan-2-yl)- N ′-(trifluoromethanesulfonyl) acetimidamide molecules are linked by intermolecular hydrogen bonds R–NH···O=S. However, according to the quantum-chemical calculations data, the Tf-NH···O=S type H-bonds turn out to be stronger by 3 kcal/mol when dimers are formed. The relative energy of formation of (2 S ,7 S )- N -7-iodobicyclo[2.2.1]heptan-2-yl)- N ′-(trifluoromethanesulfonyl) acetimidamide self-associates is ~10 kcal/mol.
ISSN:1070-3632
1608-3350
DOI:10.1134/S107036322105008X