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A density functional theory approach toward substituent effect in Meerwein–Eschenmoser–Claisen rearrangement

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Abstract

B3LYP/6-31 G(d) level of theory has been used for the examination of substituent effect in the concerted step of the Meerwein-Eschenmoser-Claisen rearrangement. In this regard, the effect of NO2 and NH2 groups in different positions has been investigated. The obtained results show that substituent effect is very sensitive to its position and configuration. Electron withdrawing and electron donating groups in different positions and various configurations show different and sometimes opposite results.

The examination of substituent effect in the concerted step of the Meerwein-Eschenmoser-Claisen rearrangement

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Acknowledgments

Special thanks to Dr. Shant Shahbazian for his assistance and guidance during the study and preparing of this manuscript. We thank Professor Seik Weng Ng for making available to us his softwares and machine time facilities. The financial support of Research Council of Shahid Beheshti University is gratefully acknowledged.

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  1. Department of Chemistry, Shahid Beheshti University, G. C., P. O. Box 19396–4716, Tehran, Iran

    Rahim Ghadari & Ahmad Shaabani

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  1. Rahim Ghadari
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  2. Ahmad Shaabani
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Correspondence to Ahmad Shaabani.

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Ghadari, R., Shaabani, A. A density functional theory approach toward substituent effect in Meerwein–Eschenmoser–Claisen rearrangement. J Mol Model 18, 319–328 (2012). https://doi.org/10.1007/s00894-011-1080-x

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