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Theoretical studies on the proton-transfer reactions in propylene and pentadiene derivatives

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Abstract

Due to the insufficient understanding of the intramolecular proton-transfer reactions in the heteroatoms-substituted propylene and pentadiene, relevant geometrical, electronic, and energetic properties of propylene derivatives (1–12) and pentadiene derivatives (13–24) have been investigated theoretically. It appears that, the “enol” form is thermodynamically less stable than the corresponding tautomer except for 9, 12, and 21. Owing to the stabilization effects of the heteroatoms, the proton-transfer reactions are more favorable for the heteroatoms-substituted cases than that of the corresponding propylene or pentadiene. The proton-transfer barriers in the propylene derivatives are higher than those in the corresponding pentadiene derivatives due to the different steric conditions for the formation of transition states. These barriers have a linear correlation with the charges of their transferred hydrogen atoms. Relevant geometric and electronic variations have also been studied. Specially, H2O assists the proton-transfer reactions in propylene derivatives, but inhibits these reactions in pentadiene derivatives. The above trends are slightly changed when the polarizable-continuum-based aqueous phase is considered.

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Authors and Affiliations

  1. Department of Chemistry, ZJU-NHU United R&D Center, Zhejiang University, Hangzhou, 310027, People’s Republic of China

    Hang Sun & Haoran Li

  2. State Key Laboratory of Chemical Engineering, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310027, People’s Republic of China

    Haoran Li

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  1. Hang Sun
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  2. Haoran Li
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Correspondence to Haoran Li.

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Sun, H., Li, H. Theoretical studies on the proton-transfer reactions in propylene and pentadiene derivatives. Struct Chem 26, 587–597 (2015). https://doi.org/10.1007/s11224-014-0521-4

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