Synthesis and crystal structures of N,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate and N-iso-propyl-idene-N,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate.
Acta Crystallogr E Crystallogr Commun
; 80(Pt 5): 543-549, 2024 Apr 01.
Article
em En
| MEDLINE
| ID: mdl-38721416
ABSTRACT
Two 2,4,6-tri-methyl-aniline-based trifuloro-methane-sulfonate (tri-fluoro-methane-sulfonate) salts were synthesized and characterized by single-crystal X-ray diffraction. N,2,4,6-Tetra-methyl-anilinium tri-fluoro-methane-sulfonate, [C10H14NH2 +][CF3O3S-] (1), was synthesized via methyl-ation of 2,4,6-tri-methyl-aniline. N-Iso-propyl-idene-N,2,4,6-tetra-methyl-anilinium tri-fluoro-meth-ane-sulfonate, [C13H20N+][CF3O3S-] (2), was synthesized in a two-step reaction where the imine, N-iso-propyl-idene-2,4,6-tri-methyl-aniline, was first prepared via a dehydration reaction to form the Schiff base, followed by methyl-ation using methyl tri-fluoro-methane-sulfonate to form the iminium ion. In compound 1, both hydrogen bonding and π-π inter-actions form the main inter-molecular inter-actions. The primary inter-action is a strong N-Hâ¯O hydrogen bond with the oxygen atoms of the tri-fluoro-methane-sulfonate anions bonded to the hydrogen atoms of the ammonium nitro-gen atom to generate a one-dimensional chain. The [C10H14NH2 +] cations form dimers where the benzene rings form a π-π inter-action with a parallel-displaced geometry. The separation distance between the calculated centroids of the benzene rings is 3.9129â
(8)â
Å, and the inter-planar spacing and ring slippage between the dimers are 3.5156â
(5) and 1.718â
Å, respectively. For 2, the [C13H20N+] cations also form dimers as in 1, but with the benzene rings highly slipped. The distance between the calculated centroids of the benzene rings is 4.8937â
(8)â
Å, and inter-planar spacing and ring slippage are 3.3646â
(5) and 3.553â
Å, respectively. The major inter-molecular inter-actions in 2 are instead a series of weaker C-Hâ¯O hydrogen bonds [Câ¯O distances of 3.1723â
(17), 3.3789â
(18), and 3.3789â
(18)â
Å], an inter-action virtually absent in the structure of 1. Fluorine atoms are not involved in strong directional inter-actions in either structure.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Acta Crystallogr E Crystallogr Commun
Ano de publicação:
2024
Tipo de documento:
Article