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DFT molecular orbital calculations and natural bond orbital analysis of 1,2,7-thiadiazepane conformers

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Abstract

Density functional theory (B3LYP/cc-pVDZ//B3LYP/cc-pVDZ) is used to optimize the geometries of 1,2,7-thiadiazepane and natural bond orbital (NBO) analyses have been carried out employing the HF/6-31G(d,p) level using B3LYP/cc-pVDZ geometries to study the stereoelectronic effects on the stability of the stereoisomers (axial–axial, equatorial–equatorial, and axial–equatorial). The results of NBO calculations showed that the axial–axial or axial–equatorial stereoisomers are the most stable conformers, where not only the stereoelectronic effect, but also the steric repulsion significantly affects their stability.

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Acknowledgments

The authors wish to acknowledge Anna Ranson, Casa Latin-American, London, UK for reading the manuscript and Dr. Louise S. Price, UCL, London, UK for providing valuable suggestions.

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  1. Department of Chemistry, Islamic Azad University, Babol Branch, Babol, Iran

    Mina Haghdadi

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  1. Mina Haghdadi
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Correspondence to Mina Haghdadi.

Electronic supplementary material

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706_2013_1042_MOESM1_ESM.doc

Geometrical parameter, zero-point, absolute energies, and NBO stabilization energies of optimized conformers are available in supporting tables (DOC 999 kb)

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Haghdadi, M. DFT molecular orbital calculations and natural bond orbital analysis of 1,2,7-thiadiazepane conformers. Monatsh Chem 144, 1653–1661 (2013). https://doi.org/10.1007/s00706-013-1042-3

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  • DOI: https://doi.org/10.1007/s00706-013-1042-3

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