Iodine Bonding Stabilizes Iodomethane in MIDAS Pesticide. Theoretical Study of Intermolecular Interactions between Iodomethane and Chloropicrin
The results are reported of a theoretical study of iodomethane (H3C-I, 1) and chloropicrin (Cl3C-NO2, 2), of the heterodimers 3-6 formed by aggregation of 1 and 2, and of their addition products 7 and 8 and their possible fragmentation reactions to 9-18. Mixtures of iodomethane and chloropicrin are not expected to show chemistry resulting from their reactions with each other. The structures and stabilities are discussed of the iodine-bonded molecular aggregates (IBMA) 3 and 4 and of the hydrogen- and iodine-bonded molecular aggregates (IHBMA) 5 and 6. The mixed aggregates 3-5 are bound on the free enthalpy surface relative to the homodimers of 1 and 2, and the IBMA structures 3 and 4 are most stable. This result suggests that the mixture of chloropicrin and iodomethane in the pesticide Midas is a good choice to reduce the volatility of iodomethane because of thermodynamically stabilizing iodine bonding.
R. Glaser and K. Prugger, "Iodine Bonding Stabilizes Iodomethane in MIDAS Pesticide. Theoretical Study of Intermolecular Interactions between Iodomethane and Chloropicrin," Journal of Agricultural and Food Chemistry, vol. 60, no. 7, pp. 1776-1787, American Chemical Society (ACS), Feb 2012.
The definitive version is available at https://doi.org/10.1021/jf2037906
Keywords and Phrases
chloropicrin; halogen bonding; intermolecular bonding; methyl iodide; pesticide; soil fumigant; UHF instability
International Standard Serial Number (ISSN)
Article - Journal
© 2012 American Chemical Society (ACS), All rights reserved.
01 Feb 2012