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Structure of porphyrin H-associates, inverted porphyrinoids, and corroles with N,N-dimethylformamide

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Abstract

By means of quantum-chemical calculations (DFT B3LYP, CC-pVDZ basis set) the previously proposed structure and interaction energy of the components of H-associates of meso-tetraphenylporphyrin and its analogues (comp. I–III) with N,N-dimethylformamide (DMF) of the 1:1 composition is confirmed theoretically for the first time. In the ability to form H-associates involving NH bonds of intramolecular coordination centers (CCs) the macrocycles can be ordered as: I ≈ III b < III a < II. Tautomer III b is shown to form an H-associate involving an outer-cyclic 2NH proton, and a macrocycle of corrole II has a strong intramolecular H bond in CC. One of the factors determining the NH activity of macrocycles is the degree of a deviation of the intracyclic NH protons from the plane of the molecule in its non-associated form.

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Authors and Affiliations

  1. Research Institute of Macroheterocyclic Compounds, Ivanovo State University of Chemical Technology, Ivanovo, Russia

    D. B. Berezin

  2. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, Ivanovo, Russia

    M. A. Krest’yaninov

Authors
  1. D. B. Berezin
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  2. M. A. Krest’yaninov
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Correspondence to D. B. Berezin.

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Original Russian Text © 2014 D. B. Berezin, M. A. Krest’yaninov.

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Translated from Zhurnal Strukturnoi Khimii, Vol. 55, No. 5, pp. 868–876, September–October, 2014.

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Berezin, D.B., Krest’yaninov, M.A. Structure of porphyrin H-associates, inverted porphyrinoids, and corroles with N,N-dimethylformamide. J Struct Chem 55, 822–830 (2014). https://doi.org/10.1134/S0022476614050047

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