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Investigation of Halogen Bond Interactions of Chiral Molecules Using Infrared, Vibrational Circular Dichroism, NMR, UV-vis Spectroscopy and Density Functional Theory Calculations

  • Author / Creator
    Moazeni, Amin
  • This PhD thesis shows the application of different spectroscopic and theoretical tools
    to probe the extent and possible interaction between various Lewis acids (halogen
    bond donor) and Lewis bases (halogen bond acceptors). Vibrational circular
    dichroism (VCD) that is the chiral version of infrared (IR) spectroscopy is able to
    provide valuable information about the absolute configuration of a chiral molecule in
    the solution when coupled with theoretical calculations. This technique is also
    sensitive to intermolecular interactions. Since the strength and level of interaction
    between the halogen bond donors and halogen bond acceptors is unknown to us we
    have also decided to utilize other spectroscopy techniques such as 19F-NMR, 1HNMR, and UV-vis spectroscopy.
    In chapter 3, I studied the formation of the halogen bond between 4-benzyl-
    1,3-thiazolidine-2-one (NOS) and iodine. In order to probe the interaction between
    the two molecules I used FT-IR, VCD, 1H-NMR, and UV-vis spectroscopy
    techniques. Density Functional Theory (DFT) calculations allowed me to find out
    what would be the conformers of the interacting species and which ones would
    contribute to the formation of final complexes. This study concluded with no
    interaction between the two species.
    In chapter 4, I studied the formation of the halogen bond between 4-benzyl-
    1,3-thiazolidine-2-thione (NSS) and iodine in the solution using FT-IR, VCD, 1HNMR, and UV-vis spectroscopy techniques. DFT simulations were carried out to find
    out the most stable conformers of the interacting species and the formation of final
    complexes. This study concluded with discovery of a new halogen bond interaction
    motif between the two species.
    In chapter 5, I studied the formation of halogen bond between 4-benzyl-1,3-
    thiazolidine-2-one (NOS) and iodopentafluorobenzene (F5BnI) in the solution using
    FT-IR, VCD, 1H-NMR, and 19F-NMR spectroscopy. Sensitivity of the VCD and 19FNMR spectroscopy allowed me to monitor small changes in the spectra of interacting
    species. Consequently with the aid of DFT simulations I was able to suggest the most
    probable conformer for the interaction between the donor and acceptor species.
    In chapter 6, I studied the formation of halogen bond between 4-benzyl-1,3-
    thiazolidine-2-thione (NSS) and iodopentafluorobenzene (F5BnI) in the solution using
    FT-IR, VCD, 1H-NMR, and 19F-NMR spectroscopy. 19F-NMR signals does not
    suggest a strong interaction between the two species due to the low change in the
    chemical shift. Despite the fact that the interaction between these species is weak, we
    were able to collect signals from the VCD machine which together with the DFT data
    enabled us to suggest a possible structure in the formation of the complex.

  • Subjects / Keywords
  • Graduation date
    Fall 2023
  • Type of Item
    Thesis
  • Degree
    Doctor of Philosophy
  • DOI
    https://doi.org/10.7939/r3-g25t-6684
  • License
    This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.