Przemysl Chemiczny, Vol.85, No.8-9, 602-604, 2006
Synthesis and crystal structure of 1-benzyl-3-cyclododecylo,xymethyl-2-methylimidazolium acetate
in a novel synthesis, 1-benzyl-2-methytimidazole quaternized with chloromethylcyclododecyl ether (prepd. by passing HCl through cyclododecanol + HCOH) gave 1-benzyl-3-cyclododecyloxymethyl-2-methylmidazolium chloride in 98% yield. The chloride was treated in water with AcONa in 20% excess to yield the acetate in 96.4% yield. (plates from MeOH). The dihydrate was centrosymmetric triclinic, space group P-1, and its unit cell consts. were: a 1.0700, b 1.4032, c 1.8294 nm, alpha 79.12, beta 85.27, gamma 87.99 degrees, cell vol., 2.6972 nm(3), calcd. d. 1.058 g/cm(3) at 293K. All bond lengths, valence and torsion angles, non-H atom coordinates, and equiv. isotropic displacements were calcd. The inbuilt H2O mols. form strong (with carboxyl O atom) and weak H-bonds and interact with the imidazolium ring's N atom at the benzyl substituent.