2,4,6-Trimethylphenyl isocyanide

Abstract

The title compound, C(10)H(11)N, displays a crystallographic mirror plane that incorporates all the non-H atoms, as well as the H atoms attached to the aromatic ring. The isocyano group is almost linear and shows an N[triple bond]C bond distance of 1.158 (3) A.

Synthesis of poly(quinoxaline‐2,3‐diyl)s with alkoxy side chains by aromatizing polymerization of 4,5‐dialkoxy‐substituted 1,2‐ diisocyanobenzenes

“…The NC bond distances (1.163-1.166 Å) are slightly longer than those found in aromatic monoisocyanides (1.153-1.163 Å). 13 It is known that the distance of NBC bonds in monoisocyanobenzene derivatives is not strongly influenced by the electronic density of the aromatic ring (p-isocyanoaniline: 1.158 Å, 14 pentafluorophenyl isocyanide: 1.159 Å 15 ) or a methyl group at the ortho position (2,4,6-trimethylphenyl isocyanide: 1.158 Å 13 ). The elongation of the NBC bond may arise from appreciable contributions of a resonance structure containing C¼ ¼N þ ¼ ¼C form, which reduces the NBC bond order (Fig.…”

“…1 H NMR data are reported as follows: chemical shift in ppm downfield from tetramethylsilane (d scale), multiplicity (s ¼ singlet, d ¼ doublet, t ¼ triplet, m ¼ multiplet, and br ¼ broad), coupling constant (Hz), and integration. 13 C NMR chemical shifts are reported in ppm downfield from tetramethylsilane (d scale). All 13 C NMR spectra were obtained with complete proton decoupling.…”

“…The N≡C bond distances (1.163-1.166 Å) are slightly longer than those found in aromatic monoisocyanides (1.153-1.163 Å). 13 It is known that the distance of N≡C bonds in monoisocyanobenzene derivatives is not strongly influenced by the electronic density of the aromatic ring (p-isocyanoaniline: 1.158 Å, 14 pentafluorophenyl isocyanide: 1.159 Å 15 ) or a methyl group at the ortho position (2,4,6-trimethylphenyl isocyanide: 1.158 Å 13 ).…”

Polyfunctional Energetic Nitrates Derived from Tris(hydroxymethyl)aminomethane (Tris)

“…The direct nitration of BisTris in a mixture of glacial acetic acid, acetic anhydride, and white fuming nitric acid, yielded bis(2-nitratoethyl)amino-tris(nitratomethyl)methane (1) in moderate yields. Treatment of Tris with diethyl malonate in methanol heated to reflux resulted in the formation of N,N′-bis[tris(hydroxymethyl)methyl]malonamide, [7] which upon nitration in white fuming nitric acid resulted in the formation of N,N′-bis[tris-(nitratomethyl)methyl]malonamide (2). Tricine was nitrated in pure white fuming nitric acid, and the aqueous work-up gave the nitrate N-[tris(nitratomethyl)methyl]nitramino glycine (3) as a pure compound without further purification.…”

“…The starting material N,N′-bis[tris(hydroxymethyl)methyl]malonamide [7] (620 mg, 2 mmol) was added dropwise to ice-cold white fuming nitric acid (5 mL). After the solution was stirred at 0°C for 1 h, it was poured on ice to give a colorless precipitate.…”