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A comparative study of two-ring resonance-assisted hydrogen bond systems

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Abstract

Two-ring resonance-assisted hydrogen bond (RAHB) systems can be obtained by merging two cis enol ring of malondialdehyde with different orientations. In the present work, a comparative theoretical study of all of the possible two-ring RAHB systems, 2,3-dihydroxy-2-butene-4-dial (DBD), 1,5-dihydroxy-1,4-diene-3-pentanone (DDP) and 2-dihydroxy-methylene-propanediol (DMP), was carried out. Also, the influence of the co-existence of two RAHB rings on the molecular structures, intramolecular hydrogen bond (IMHB) and the π-electron delocalization (π-ED) was investigated. In this regard, ab initio calculations on the various equilibrium conformations of DBD, DDP and DMP at MP2/6-311++G(d,p) level of theory have been performed and the IMHB strength of model compounds by different descriptors such as geometrical, topological, molecular orbital, spectroscopic and energetic parameters was evaluated. Then, the π-ED of DBD, DDP and DMP was estimated by using a variety of indicators, such as geometrical factor of Gilli (λ), the harmonic oscillator model of aromaticity, the nucleus-independent chemical shift, the para delocalization index, the average two-center index, the aromatic fluctuation index. Finally, based on the computational results, it was found that the strength of IMHB and significance of π-ED in two-ring RAHB systems are strongly related to the relative flow of π-electrons in two rings. In other words, the parallel flows of π-electrons in DMP and DDP increase the IMHB strength and π-ED, while opposite flow of π-electrons in DBD decreases the IMHB strength and π-ED.

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Acknowledgments

The authors gratefully thank University of Sistan and Baluchestan (USB) for the financial supports.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran

    A. Nowroozi, S. Rahmani, A. Eshraghi & K. Shayan

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  1. A. Nowroozi
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  2. S. Rahmani
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  3. A. Eshraghi
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  4. K. Shayan
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Correspondence to A. Nowroozi.

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Nowroozi, A., Rahmani, S., Eshraghi, A. et al. A comparative study of two-ring resonance-assisted hydrogen bond systems. Struct Chem 27, 829–838 (2016). https://doi.org/10.1007/s11224-015-0637-1

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  • DOI: https://doi.org/10.1007/s11224-015-0637-1

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