Remediation of Methyl Iodide in Aqueous Solution and Soils Amended with Thiourea

2004 ◽  
Vol 38 (4) ◽  
pp. 1188-1194 ◽  
Author(s):  
Wei Zheng ◽  
Sharon K. Papiernik ◽  
Mingxin Guo ◽  
Scott R. Yates
Keyword(s):  
Aqueous Solution ◽  
Methyl Iodide

Quaternary Nitrogen Heterocycles. IV. The 1-Methyl-4-nitroquinolinium and 4,4-Diiodo-1,1-dimethy1-1,4-dihydroquinolinium Cations, Two Methylation Products of 4-Nitroquinoline and their Reactions in Aqueous Solutions

1974 ◽  
Vol 52 (6) ◽  
pp. 951-961 ◽  
Author(s):  
John W. Bunting ◽  
William G. Meathrel
Keyword(s):  
Aqueous Solution ◽  
Methyl Iodide ◽  
Alkaline Solution ◽  
Silver Iodide ◽  
Spectroscopic Data ◽  
Nitrogen Heterocycles ◽  
Aqueous Alkaline Solution ◽  
Quaternary Nitrogen ◽  
Unexpected Product ◽  
Species Being

Methylation of 4-nitroquinoline with methyl fluorosulfonate ("magic methyl") gives the expected 1-methyl-4-nitroquinolinium fluorosulfonate. However, methylation with methyl iodide gives an unexpected product (C11H12I3N) which is shown to be 4,4-diiodo-1,1-dimethyl-1,4-dihydroquinolinium iodide. This latter salt readily loses a molecule of methyl iodide in aqueous alkaline solution and forms 4-hydroxy-4-iodo-1-methyl-1,4-dihydroquinoline. This latter product reacts in aqueous solution with excess silver iodide or bromide in the presence of silver nitrate to give 3-iodo-1-methyl-4-quinolone or the corresponding 3-bromo derivative. The 1-methyl-4-nitroquinolinium cation readily forms a pseudobase in aqueous solution (pKROH = 5.31; pKRO− = 10.95 ). Kinetic and spectroscopic data are consistent with the predominant neutral pseudobase species being 4-hydroxy-1-methyl-4-nitro-1,4-dihydroquinoline, while the predominant pseudobase anion is the alkoxide ion of 2-hydroxy-1-methyl-4-nitro-1,2-dihydroquinoline.

Kinetic deuterium isotope effect in the reaction of methyl iodide with thiosulfate ion in aqueous solution

1970 ◽  
Vol 48 (9) ◽  
pp. 1452-1455
Author(s):  
Alfred V. Willi ◽  
Chong Min Won
Keyword(s):  
Aqueous Solution ◽  
Gas Phase ◽  
Isotope Effect ◽  
Methyl Iodide ◽  
Isotope Effects ◽  
Force Constants ◽  
Deuterium Isotope Effect ◽  
Model Calculations ◽  
Bending Force ◽  
Reaction Vessels

The kinetic deuterium isotope effect in the reaction of methyl iodide with thiosulfate ion in aqueous solution has been determined as follows: kH/kD (per 3D) = 0.966 (+0.02°), 0.968 (+10.00°), 0.970 (+19.98°). Kinetic experiments have been carried out in reaction vessels with no gas phase. The experimental data are compared with results of model calculations of isotope effects from force constants. Excellent agreement between experimental and calculated isotope effects may be obtained with the following values of the transition state bending force constants: fHCI = 0.295 mdyn Å, fHCS = 0.300 to 0.320 mdyn Å. These values are equal to 50–65% of the corresponding bending force constants in stable molecules.

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