New oxyalkyl derivatives of trifluoromethanesulfonamide: Dynamic rivalry between different types of chain and cyclic associates in different phase states

New derivatives of triflamide, N-{[5-(iodomethyl)-4-(trifluoromethylsulfonyl)morpholin-3-yl]methyl}triflamide 1, N,N’-(3-ethoxypropane-1,2-diyl)bis(triflamide) 2 and N,N’-(3-phenoxypropane-1,2-diyl)bis(triflamide) 3 have been synthesized and the X-ray crystal structure of 1 determined. The monomeric units of compounds 1–3 form supramolecular structure by self-assembling via intermolecular hydrogen bonding of different type. The rivalry between the NH⋯O = S and NH⋯O hydrogen bonded associates was studied employing the methods of IR spectroscopy in different phases (gas, crystal, liquid, plastic phase, solution, glassified solution) at different temperatures. Theoretical calculations of the monomers and cyclic and chain dimers formed by different conformers of compounds 1–3 have been performed using DFT and MP2 methods as well as QTAIM and molecular electrostatic potential analyses. The combined experimental and theoretical results allowed determining the structure of the species predominating in different states at different temperatures. [Display omitted] •New Oxyalkyl Derivatives of Triflamide are synthesized.•X-ray structure of N-{[5-(iodomethyl)-4-(triflyl)morpholin-3-yl]methyl}triflamide is determined.•H-bonded associates of new compounds are investigated in different phases by IR spectroscopy and DFT and MP2 calculations.