Carbon-carbon coupling reactions of medium-sized nitrogen-containing dications

J Phys Chem A. 2010 May 20;114(19):5989-96. doi: 10.1021/jp100852q.

Abstract

The reactivity of molecular dications C(m)H(n)N(2+), generated by (dissociative) double ionization of different heteroaromatic compounds, with methane, ethane, and nitrogen is investigated using a triple-quadrupole mass spectrometer. About a quarter of the set of dications studied undergo carbon-carbon coupling reactions with methane, whereas only nonspecific reactions leading to the formation of monocations (such as proton-, electron- and hydride transfer as well as Coulomb explosions) occur in the presence of either ethane or nitrogen. Here, we report the reactivity observed for 42 different C(m)H(n)N(2+) dications formed via electron ionization of eleven different heteroaromatic precursors. The potential relevance of these results is discussed in the context of the growth of hydrocarbon species and their nitrogen-containing homologues at extremely low temperatures and pressures, such as in interstellar environments or the ionospheres of planets and moons, Saturn's moon Titan in particular.