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Isomerization energies and surface electrostatic potential analyses on nitriles and isocyanides

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Abstract

Isocyanide-nitrile rearrangement has long been a continuing and interesting topic. A series of nitriles and isocyanides with the substituents of R = -AlH2, -BeH, -BH2, -C≡CH, -CF3, -CH3, -Cl, -C≡N, -COOH, -F, -H, Li, -MgH, -Na, -NH2, -NO2, -OH, -PH2, -SH, -SiH3, and -CH = CH2 were investigated systematically based on full optimization at B3LYP-D3(BJ)/def2-QZVP level, and the isomerization energies from R–C≡N to:C = N-R were estimated. The substituent effect and bonding characters were analyzed by surface ESP colored van der Waals surfaces in conjunction with the global and local electrostatic extrema.

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Funding

This work was supported by the Natural Science Foundation of Shandong Province (ZR2017LB010) and the Science and Technology Planning Project (Guidance Plan) of Tai’an City (No. 2018GX0041).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Taishan University, Tai’an, 271000, Shandong, China

    Yanyun Zhao & Xueli Cheng

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  1. Yanyun Zhao
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  2. Xueli Cheng
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Contributions

Yanyun Zhao: Software; Formal analysis; Investigation; Writing, original draft. Xueli Cheng: Conceptualization; Methodology; Software; Writing, original draft and editing; Management and responsibility for the research activity planning and execution.

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Correspondence to Xueli Cheng.

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Zhao, Y., Cheng, X. Isomerization energies and surface electrostatic potential analyses on nitriles and isocyanides. J Mol Model 27, 257 (2021). https://doi.org/10.1007/s00894-021-04870-6

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  • DOI: https://doi.org/10.1007/s00894-021-04870-6

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