Date Published: June 01, 2012
Publisher: International Union of Crystallography
Author(s): Ioannis Tiritiris, Willi Kantlehner.
The reaction of 3,3,3-tris(dimethylamino)-1-phenylprop-1-yne with bromine in pentane yields the title compound, C13H17N2+·Br−. The acetylenic bond distance [1.197 (2) Å] is consistent with a C C triple bond. The amidinium C=N bonds [1.325 (2) and 1.330 (2) Å] have double-bond character and the positive charge is delocalized between the two dimethylamino groups.
For the synthesis of alkynyl orthoamides and acetylenic amidinium salts, see: Weingärtner et al. (2011 ▶). For the synthesis of vinylogous guanidinium iodides and bromides, see: Kantlehner et al. (2012 ▶). For the crystal structure of N,N,N′,N′,N′′,N′′,N′′′,N′′′-octamethyl-(but-2-yne)-bis(amidinium)-bis(tetrafluoridoborate), see: Drandarov et al. (2012 ▶).