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Theoretical Investigation of Hydrogen Bonding Effects on Acidity Enhancement of Beta Diketones in Gas and Solution Phase

Rahimi, Mona | 2017

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  1. Type of Document: M.Sc. Thesis
  2. Language: Farsi
  3. Document No: 50339 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Fattahi, Alireza; Mahmoodi Hashemi, Mohammad
  7. Abstract:
  8. Hydrogen bonding is an important weak interaction encountered in gas and liquid, as well as solid phase. The hydrogen bond plays a very vital role in many life processes and is one of the most frequently used terms in chemistry and biology. Beta diketones have several applications in organic, inorganic and analytical chemistry. Different substituents can affect the acidity of beta diketones. Investigation have shown that hydroxyl function group can increase the acidity of many organic molecules through interamolecular hydrogen bonding. The goal of this project is to investigate the acidity of hydroxyl containing beta diketones in the gas and solution phase. All the gas phase optimizations and energy calculation were performed at the DFT/B3LYP/6-31G+(d) level of density functional theory (DFT). The solution phase calculations were performed using PCM method. Linear correlation between gas phase acidity and pKa in solution phase was obtained and can be used for prediction of pKa for other alcoholic models. Also, in order to study the nature of effective bonds in interactions, QTAIM and NBO analyses are used. As expected, interamolecular hydrogen bonds in these models shows drastic influence in acidities of these molecules
  9. Keywords:
  10. Acidity ; Density Functional Theory (DFT) ; Hydrogen Bond ; Functional Group ; Beta-Diketone

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