The only product resulting from the methylation of DEA was Ch (20% yield, based on conversion of DEA, of which 80% remained). The assignment of Ch was made by comparison with a spectroscopic standard in aqueous phosphate buffer at pH 7.4. Products resulting from the methylation of nucleophiles other than DEA (namely ferrocyanide (a product of the system), water, and cyanide) included [Fe(CN) 5 CNMe] 3-, methanol, and acetonitrile. The assignment of these species was made based on their reported chemical shifts in D Methylamine hydrochloride (13.5 mg, 0.2 mmol) was dissolved in H 2 O (2.0 mL) and the pH of the solution was adjusted to 10.0. Sodium cyanide (9.8 mg, 0.2 mmol) was added followed by MEA (1.6 μL, 0.02 mmol) and the pH of the mixture was readjusted to 10.0. Sodium nitroprusside dihydrate (59.6 mg, 0.2 mmol) was then added and the mixture was stirred vigorously at room temperature while bubbles of nitrogen gas evolved. After 24 hours, 450 μL of the mixture was removed for analysis by H-NMR spectroscopy. To this aliquot, 50 μL of 1.0 M NaH 2 PO 4 in D 2 O was added and the pH of the mixture was adjusted to 7.4 before to the NMR spectrum was acquired.