Menschutkin reactions of bicyclic aliphatic amines and of pyridine derivatives with methyl iodide. Extended Brönsted treatements and isokinetic relationships in acetonitrile–methanol

Non-covalent interactions between iodo-perfluorocarbons and hydrogen bond acceptors

“…3d), but the correlations are not strong. 11 Fig. 4 compares the molecular electrostatic potential surfaces of 1 and 3.…”

An experimental, computational, and uncertainty analysis study of the rates of iodoalkane trapping by DABCO in solution phase organic media

“…Based on the rate constants reported in the literature, 7 the first substitution reaction of MeI + DABCO in AcN ( k 1 ca. 2.05 M −1 s −1 at 30 °C) was expected to be too fast to be reliably followed by NMR spectroscopy; however, kinetics data could be recorded for the reaction run in methanol ( k 1 ca.…”

“…2,3 Here, we have employed this technique to follow the time dependent behaviour of the reactants, intermediates and products 3–5 of the single and double S N 2 substitution of 1,4-diazabicyclo[2.2.2]octane (DABCO) reaction with iodoalkanes in solution. 6–8 DABCO is a tertiary amine and strong nucleophile. This Menshutkin reaction is of interest, not only from the fundamental science perspective, 6–25 but also for nuclear safety applications, since DABCO-saturated materials are used in reprocessing plant ductwork filters, 26–30 and to clean up iodine spills from nuclear reactors.…”

“…6–8 DABCO is a tertiary amine and strong nucleophile. This Menshutkin reaction is of interest, not only from the fundamental science perspective, 6–25 but also for nuclear safety applications, since DABCO-saturated materials are used in reprocessing plant ductwork filters, 26–30 and to clean up iodine spills from nuclear reactors. 31–36 During nuclear accidents, volatile iodine radioisotopes can be released as inorganic iodines (I 2 , I x O y ), and as organic iodides that are created via reactions with hydrocarbons and other volatile organic chemicals.…”

“…Here we present a multifaceted approach to determining kinetics and thermodynamic parameters for iodoalkane-DABCO S N 2 reactions. Unlike previously reported DABCO reaction investigations, 6–8 we consider both first and second substitutions with iodoalkanes. We report reaction enthalpies, activation energies and kinetics for the first and second substitution of DABCO with iodomethane and 1-iodobutane in the perdeuterated solvents acetonitrile-d 3 (AcN), dimethyl sulfoxide-d 6 (DMSO), and methanol-d 4 (CD 3 OD).…”