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Density functional study on the tautomerism of pyrano[2,3-d]pyrimidine derivative: intramolecular and intermolecular proton transfer

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Abstract

The proton transfer reaction mechanisms in the anhydrous and monohydrated forms of 7-amino-6-cyano-5-benzene-5H-pyrano[2,3-d]pyrimidine-2,4(1H,3H)-diones on the transition state structures have been carried out in the gas phase using the B3LYP density functional method. For the reaction, three possible mechanisms are considered and three pathways are subsequently discussed. Meanwhile, the assistant effects of water molecules in the 1st path, which is considered as the best way of proton transfer, have been discussed in detail with the number of water molecules increasing. Results reveal that water molecules hold a strong catalysis effect on the proton transfer, and the polar solvent is favorable to the stability of complexes.

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Acknowledgement

The authors thank the National Natural Science of Foundation of China (No. 21376220) and the Natural Science Foundations of Zhejiang Province (No. LY12B03008 and LY16B060009).

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Authors and Affiliations

  1. State Key Laboratory Breeding Base for Green Chemistry Synthesis Technology, College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou, 310014, People’s Republic of China

    Jianqin Hu, Litao Chen & Chunan Ma

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  1. Jianqin Hu
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  2. Litao Chen
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  3. Chunan Ma
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Correspondence to Litao Chen.

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Hu, J., Chen, L. & Ma, C. Density functional study on the tautomerism of pyrano[2,3-d]pyrimidine derivative: intramolecular and intermolecular proton transfer. Res Chem Intermed 43, 4795–4812 (2017). https://doi.org/10.1007/s11164-017-2912-9

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