Theoretical study of solvent effect on diastereoselectivity in protonation of methyl 3-fluorobutanoate anion by ethanol: Application of the 3D-RISM theory
作者： Yasuhiro Ikuta , Yutaka Maruyama , Fumio Hirata , Shuji Tomoda
DOI: 10.1016/J.THEOCHEM.2006.11.036
关键词:
摘要: The H/D exchange reaction of carbonyl compounds is one the most important reactions in synthetic organic chemistry as well biochemistry. In present study, 3D-RISM theoretical model has been used to examine high diastereoselectivity and solvent effects protonation methyl 3-fluorobutanoate anion by ethanol. analysis along IRC coordinates clearly suggested that not only molecules stabilize system throughout entire process, but also stabilization mechanism operates so minimize energy difference between two diastereofacial processes. processes ground state carries directly through transition state. This strongly should be determined essentially Confirmative evidence for this conclusion was obtained EFOE (exterior frontier orbital extension model) model.
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