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Computational investigation on the intramolecular resonance-inhibited hydrogen bonding: a new type of interaction versus the RAHB model

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Abstract

A new type of intramolecular interaction is introduced by choosing a tautomer of β-aminoacrolein as a model. The term “resonance-inhibited hydrogen bond (RIHB)” is considered to describe this interaction. The intramolecular hydrogen bond (IMHB) energy values are estimated at the B3LYP and MP2 levels of theory. The QTAIM analysis and other descriptors are employed to corroborate the obtained results. According to the results, one predicts that the IMHB strength in the RIHB benchmark system is higher than in its corresponding saturated analog, which is attributed to the planarity imposed on the molecule framework by the unsaturation. Fixing the planarity parameter during the comparison, we observe that the reverse resonance decreases the IMHB strength compared to the saturated corresponding counterpart. All of the measured parameters are compared to those of the resonance-assisted hydrogen bond analog revealing the important role of the resonance direction in strengthening or weakening of the IMHB.

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Acknowledgments

The authors 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

    Ehsan Masumian & Alireza Nowroozi

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  1. Ehsan Masumian
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  2. Alireza Nowroozi
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Correspondence to Ehsan Masumian.

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Masumian, E., Nowroozi, A. Computational investigation on the intramolecular resonance-inhibited hydrogen bonding: a new type of interaction versus the RAHB model. Theor Chem Acc 134, 82 (2015). https://doi.org/10.1007/s00214-015-1683-x

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