Computational investigations of reactivity and selectivity in addition reactions
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Date
2018-12
Authors
Singh, Simarpreet
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Abstract
The development and application of density functional theory (DFT) on real chemical
systems has allowed experimentalists to use computational chemistry, without an understanding of mathematical details behind it, as a tool alongside experimental techniques in elucidation of reaction mechanisms.
In chapter 2, DFT methods are utilized to investigate the regio- and stereo-selectivity of
organocatalytic asymmetric ε-functionalization of furfural derivatives via trienamine activation. The role of the bifunctional aminocatalyst with hydrogen bonding abilities for the observed selectivity was investigated. The transition states were also calculated to understand the experimental results. Other heterocyclic such as thiophene, pyrrole and cyclopentadiene were also investigated to understand the role of heteroatom on reactivity of trienamine.
In chapter 3, DFT methods were used to understand the effect of chain length on reactivity of S-alkyl-thiatriazine scaffolds. The competition between inter- and intra-molecular substitutionreactions was explored. The conformations of S-alkyl-thiatriazine and barrier heights of both pathways played important roles for preference of one reaction over another.
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Keywords
Density Functional Theory, Organocatalysis, Asymmetric Synthesis