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    E Z Stereoisomerization in Methylene bis-Dithiocarbamate and N,N,S Trimethyldithiocarbamate

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    2003_PharrC_THS_000845.pdf (2.536Mb)
    Author
    Pharr, Caroline; Thorburn, John
    Advisor
    Ron Wilde; Jon Salzsieder; Debra Bernardi
    Date of Issue
    2003-04-01
    Subject Keywords
    trimethyldithiocarbamate, methylene bis-dithiocarbamate, selective inversion recovery
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    URI
    https://scholars.carroll.edu/handle/20.500.12647/179
    Title
    E Z Stereoisomerization in Methylene bis-Dithiocarbamate and N,N,S Trimethyldithiocarbamate
    Type
    thesis
    Abstract
    Rates of rotation about the carbon-nitrogen partial double bond in N,N,Strimethyldithiocarbamate (1) and methylene bis-dithiocarbamate (2) were measured by the dynamic NMR technique known as selective inversion recovery. Free energies of activation (AG*) for the rotational barrier about the carbon-nitrogen partial double bond in compounds 1 and 2 were determined in a variety of solvents. Compound 1 was found to have a lower rotational barrier than compound 2. As solvent polarity increased, an increase in rotational barrier was observed. Contrary to expectations, hydroxylic solvents lowered the rotational barrier for compounds 1 and 2 based on their increased solvent polarity and hydrogen bonding capabilities. These results have implications for determining switching rates in dithiocarbamate chiroptical switches.
    Degree Awarded
    Bachelor's
    Semester
    Spring
    Department
    Chemistry & Physics
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    • Chemistry and Physics Undergraduate Theses

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