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Acid‐base properties and supramolecular structure of N ‐[(hydroxymethyl)triazolyl]triflamides: DFT, ab initio, and FTIR study
Author(s) -
Shainyan Bagrat A.,
Chipanii.,
Oznobikhina Larisa P.,
Meshcheryakov Vladimir I.
Publication year - 2017
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3623
Subject(s) - chemistry , hydroxymethyl , hydrogen bond , conformational isomerism , intramolecular force , molecule , density functional theory , intermolecular force , ab initio , supramolecular chemistry , atoms in molecules , infrared spectroscopy , crystallography , computational chemistry , stereochemistry , organic chemistry
For N ‐{[2‐(hydroxymethyl)‐2 H ‐1,2,3‐triazolyl‐4‐yl]methyl}triflamide 1 , N ‐{[2‐(hydroxymethyl)‐2 H ‐1,2,3‐triazolyl‐4‐yl]methyl}‐N‐phenyltriflamide 2 , and N , N ‐bis{[2‐(hydroxymethyl)‐2 H ‐1,2,3‐triazolyl‐4‐yl]methyl}triflamide 3 , the proton affinities of the triazole nitrogen atoms and the hydroxy and sulfonyl oxygen atoms as well as the energies of formation of the conformers with intramolecular H‐bonds and dimers with intermolecular NH⋯N, OH⋯N, OH⋯O═S, and NH⋯O═S H‐bonds were calculated by density functional theory and second‐order Møller‐Plesset perturbation methods. Quantum Theory of Atoms in Molecules analysis was performed to investigate the nature of H‐bonds. According to Fourier transform infrared spectroscopy , in CH 2 Cl 2 solution, the monomeric molecules of 1 to 3 exist in the equilibrium with cyclic dimers having the OH⋯N hydrogen bonds.