Organic Chemistry in the Absence of Hydrogen
Even should hydrogen be absent, classes of species known as chlorocarbons, cyanocarbons (and other types of carbon nitrides), fluorocarbons, nitrocarbons and oxocarbons (and other types of carbon oxides) are well-represented in the chemical literature. Examples for CnXm include X = Cl, CCl4 (carbon tetrachloride), C19Cl15 = (C6Cl5)3C (perchlorotriphenylmethyl radical and the corresponding anion and cation) (Butin, Mohammed, & Reutov, 1978) and C60Cl30 (a “fullerene chloride”) (Papina, Luk'yanova, Troyanov, Chelovskaya, Buyanovskaya, & Sidorov, 2007); X = CN and N, [C20N8]2- = {C4[CC(CN)2]4}2-(octacyano[4]radialene dianion, and related radical anion (Blinka & West, 1983), and C3N12 = C3N3(N3)3 (cyanuric triazide (Ott& Ohse, 1921)); X = F, C2F4 (tetrafluoroethylene and its polymer PTFE (Teflon®), C6(CF3)6 (hexakis(trifluoromethyl)prismane) and its benzene and Dewar benzene valence isomers (Lemal& Dunlap, 1972); X = NO2, C2(NO2)2 (dinitroacetylene, known as a cobalt carbonyl, i.e., Co2(CO)6 complex (Windler, Zhang, Zitterbart, Piggoria, & Vollhardt, 2012) but not yet the free nitrocarbon), C8(NO2)8 (octanitrocubane) (Zhang, Eaton, & Gilardi, 2000) and C12(NO2)10 = [C6(NO2)5]2, (decanitrobiphenyl) (Nielsen, Norris, Atkins, & Vuono, 1983); X = O, CO2 and [CO3]2- (the nearly ubiquitous carbon dioxide and carbonate), C7O2 (heptahexaenedione) (Maier, Reisenauer, & Ulrich, 1991) and C12O9 = C6[C(O)OC(O)]3 (mellitic trianhydride) (Adamson & Rees, 1996) respectively. There are even a “few” bromocarbons such as C4Br4 (tetrabromobutatriene) (Liu, Li, Webb, Zhang, & Goroff, 2004), iodocarbons such as C6I6 (hexaiodobenzene (Sagl & Martin, 1988),its radical cation (Molski,et al., 2012) and its dication (Sagl & Martin, 1988) and carbon sulfides such as C6S6, benzotri(1,2)dithiete and its radical cation and anion (Sülzle, Beye, Fanghänel, & Schwarz, 1989) with X = Br, I and S respectively.