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Density functional studies of the stepwise substitution of pyridine, pyridazine, pyrimidine, pyrazine, and 1,3,5-triazine with BCO

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Abstract

The structures, stabilities, and aromaticities of a series of (BCO) n (CH)5−n N (n = 0–5), (BCO) n (CH)4−n N2 (n = 0–4), and 1,3,5-(BCO) n (CH)3−n N3 (n = 0–3) clusters were investigated at the B3LYP density functional level of theory. The most stable positional isomers of individual clusters were obtained. All of the calculated CO binding energies were positive, suggesting that the BCO-substituted species are stable. It was found that the BCO-substituted structures are much less strained than their carbocation counterparts. The negative nucleus-independent chemical shifts (NICSs) obtained show that all of the BCO-substituted species possess three-dimensional aromaticity, in good accord with the aromaticities of the corresponding hydrocarbon species.

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (no. 2103103), the Natural Science Foundation of Shandong Province (no. ZR2011EL005), and the Natural Science Foundation of Ludong University (no. LY2010006). We acknowledge the support provided by Shan Xi Normal University in relation to the calculations performed in this work.

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Authors and Affiliations

  1. School of Chemistry and Materials Science, Ludong University, Yantai, 264025, China

    Xiao-Fang Qin & Feng Wang

  2. School of Chemistry and Materials Science, Shanxi Normal University, Linfen, 041004, China

    Hai-Shun Wu

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  1. Xiao-Fang Qin
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  2. Feng Wang
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  3. Hai-Shun Wu
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Correspondence to Xiao-Fang Qin.

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Qin, XF., Wang, F. & Wu, HS. Density functional studies of the stepwise substitution of pyridine, pyridazine, pyrimidine, pyrazine, and 1,3,5-triazine with BCO. J Mol Model 20, 2079 (2014). https://doi.org/10.1007/s00894-014-2079-x

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  • DOI: https://doi.org/10.1007/s00894-014-2079-x

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