Diethylamine

Vanadium trifluoride, VF 3 , (Alfa, 98%; 0.002 mol, 0.215 g) and ethylene glycol (Fisher 99%+; 0.0032 mol, 0.2 ml) were added to 0.5 ml of a 40% solution of HF (Alfa). Diethylamine * (Sigma, 99.5%; 0.001 mol, 0.5 ml) and selenious acid (Aldrich 99.999%; 0.001 mol, 0.129 g) were added to the resultant mixture before being sealed in a teflon lined steel autoclave. This was heated at 120 °C for 4 days, then allowed to cool to ambient temperature. The final product was filtered, washed in water and allowed to dry overnight at 60 °C. Crystals were blue blocks, indicating V 4+ , of typical dimension 0.06 x 0.04 x 0.03 mm. These were separated from the bulk product, a brown powder, under an optical microscope. Crystals recovered were too scarce to be analysed using powder X-ray diffraction or to be sent for elemental analysis. * Guanidine carbonate salt (0.001 mol, 0.09 g) was used in a different experiment in place of Diethylamine and produced similar results.
Crystal data, data collection and structure refinement details are summarized in Table 1. Crystals of (I) are monoclinic, in the space group C2/c. Hydrogen atoms were located from Fourier maps and refined isotropically. publCIF

Chemicals. Acetone (HPLC grade, Caledon), hexane (HPLC grade, Caledon), xylene (reagent grade, 98.5%, EMD), deuterated chloroform (CDCl3, 99.8%, Cambridge Isotope Laboratories, Inc.), tetrahydrofuran (THF, HPLC grade, Caledon), dodecane (anhydrous, 99%, Sigma-Aldrich), ethyl ether (anhydrous, 99% Sigma-Aldrich), ethyl acetate (HPLC, 99.7% Sigma-Aldrich), and 2-dodecanone (GC grade, 97%, Sigma-Aldrich) were used as received. The chemicals hexamethylenediamine (HMDA, 98%), diethylenetriamine (DETA, 99%), triethylenetetramine (TETA, 97%), tetraethylenepentamine (TEPA, technical grade), pentaethylenehexamine (PEHA, technical grade), dibutylamine (DBA, 99.5%), octylamine (99%), N-methylsuccinimide (N-MSI, 99%), butylamine (BUA, 99%), diethylamine (DEA, 99.5%), triethylamine (TEA, 99.5%), ethylene carbonate (EC, 98%), magnesium sulfate anhydrous (97%), and activated charcoal (100 mesh) were purchased from Sigma-Aldrich and were employed without further purification. Polyisobutylene succinic anhydride (PIBSA) was supplied by Imperial Oil. The chemical composition of this sample was characterized by NMR, GPC, and FTIR analysis and found to contain on average one SA unit per 52 ± 2 isobutylene monomers. Assuming one SA moiety per chain, this PIBSA sample would have an Mn of 3,012 g.mol  equivalent to a total acid number (TAN) of 37.2 mg of KOH per gram of PIBSA.

Analytical grade 1-fluoro-2-nitro-4-trifluoromethyl benzene, piperidine, morpholine, cyclohexylamine, diethylamine, 4-bromoaniline, pyrrolidine, isonicotinoyl chloride hydrochloride, nicotinoyl chloride hydrochloride, 2-chloropyridine-3-carboxylic acid and benzoyl chloride were purchased from Sigma-Aldrich (St. Louis, MO, USA) and used without further purification. Anhydrous tin(II) chloride and triethylamine were purchased from Vetec (Rio de Janeiro, Brazil) and used as received. 1 H NMR and 13 C NMR spectra were recorded on a Varian Mercury 300 instrument (Varian, Palo Alto, CA, USA) at 300 MHz and 75 MHz, respectively, using CDCl 3 and CD 3 OD as solvents. Infrared spectra were recorded on either a Varian 660-IR, equipped with GladiATR scanning from 4000 to 500 cm -1 or a Perkin Elmer Paragon 1000 FTIR spectrophotometer (Perkin Elmer do Brasil Ltda, São Paulo, Brazil), using potassium bromide (1% v/v) disks, scanning from 600 to 4000 cm -1 . Melting points are uncorrected and were obtained with an MQAPF-301 melting point apparatus (Microquimica, Campinas, Brazil). Analytical thin layer chromatography was carried out on TLC plates covered with 60GF254 silica gel. Column chromatography was performed on silica gel (60-230 mesh). Solvents used as eluents were used without further purification.