Issue 13, 2025

Gas-phase versus crystal structure of triflamide and some of its heterocyclic derivatives

Abstract

A gas-phase electron diffraction analysis combined with mass-spectrometry (GED/MS) of (2R,9S)-trans-2,9-diiodo-13-(triflyl)-13-azabicyclo[8.2.1]tridec-5-ene was performed and the results were compared with those studied earlier by GED/MS and X-ray analysis of triflamide derivatives, that is 3,7,9-tris(triflyl)-3,7,9-triazabicyclo[3.3.1]nonane, 6-iodo-3-(triflamidomethyl)-4-triflyl-1,4,2,7-oxazadisilepane, and 2,2,4,4-tetramethyl-6,8-bis(triflyl)-3-oxa-6,8-diaza-2,4-disilabicyclo[3.2.2]nonane. In addition, the first GED study was performed for triflamide CF3SO2NH2, for which the X-ray structure has also been studied. Two conformers of the first compound with the oppositely distorted dihedral angles in the five-membered ring were identified in the gas phase, and, after careful analysis, also in the crystal. Very low barrier to interconversion (1.7 kcal mol−1) and energy difference (0.6 kcal mol−1) were calculated. In the gas phase, the S–N and S–C bonds are longer than in the crystal, clearly indicating tightening due to crystal packing effects.

Graphical abstract: Gas-phase versus crystal structure of triflamide and some of its heterocyclic derivatives

Supplementary files

Article information

Article type
Paper
Submitted
26 Dec 2024
Accepted
02 Mar 2025
First published
03 Mar 2025

Phys. Chem. Chem. Phys., 2025,27, 6523-6531

Gas-phase versus crystal structure of triflamide and some of its heterocyclic derivatives

B. A. Shainyan, A. V. Eroshin and S. A. Shlykov, Phys. Chem. Chem. Phys., 2025, 27, 6523 DOI: 10.1039/D4CP04855E

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