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1D and 3D supramolecular architectures in the salts of Meso-5,7,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane with (2E)-2-cyano-2-(hydroxyimino)acetamide and 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl) hydrazinecarboxamide sustained by charge-assisted and conventional hydrogen bonds

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Abstract

Meso-5,7,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane (tet-a) — (2E)-2-cyano-2-(hydroxyimino) acetamide (caH) (1:4) (1) is a salt [tet-aH2]2+ ·2[caH]· 2[ca]− containing both neutral and deprotonated acetamide units. The acetamide units of the two types are linked by NH⋯O and OH⋯O hydrogen bonds into negatively charged chains; the chains are connected by the macrocyclic cations to form H-bonded ribbons. Tet-a and 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazinecarboxamide (urH) form a salt of 1:2:2 stoichiometry, [tet-aH2]2+·2[ur]−·2H2O (2). In (2), the deprotonated ur− units form a negatively charged 2D network substructure, and the layers are linked by the cations and water molecules to form a 3D framework. The tetraazamacrocycle shows different modes of the protonation of amine functionalities that depend on a substrate.

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Abbreviations

Tet-a:

Meso-5,7,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane

cyclen:

1,4,7,10-tetraazacyclododecane

cyclam:

1,4,8,11-tetraazacyclotetradecane

azacyclam:

1,4,6,8,11-pentaazacyclotetradecane

caH:

(2E)-2-cyano-2-(hydroxyimino)acetamide

urH:

2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazinecarboxamide

18C6:

18-crown-6

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Authors and Affiliations

  1. Institute of Applied Physics, Academy of Sciences of Moldova, Chisinau, Moldova

    M. S. Fonari, Yu. A. Simonov & Yu. M. Chumakov

  2. Ministry of Education and Science of Ukraine, Odessa State Environmental University, Odessa, Ukraine

    E. V. Ganin

  3. A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa, Ukraine

    A. A. Yavolovskii

  4. IMEM-CNR, Parma, Italy

    G. Bocelli

  5. Department of Chemistry, Technion-Israel Institute of Technology, Haifa, Israel

    M. M. Botoshansky

Authors
  1. M. S. Fonari
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  2. Yu. A. Simonov
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  3. Yu. M. Chumakov
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  4. E. V. Ganin
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  5. A. A. Yavolovskii
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  6. G. Bocelli
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  7. M. M. Botoshansky
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Original Russian Text Copyright © 2005 by M. S. Fonari, Yu. A. Simonov, Yu. M. Chumakov, E. V. Ganin, A. A. Yavolovskii, G. Bocelli, and M. M. Botoshansky

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Translated from Zhurnal Strukturnoi Khimii, Vol. 46, Supplement, pp. S95–S101, 2005.

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Fonari, M.S., Simonov, Y.A., Chumakov, Y.M. et al. 1D and 3D supramolecular architectures in the salts of Meso-5,7,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane with (2E)-2-cyano-2-(hydroxyimino)acetamide and 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl) hydrazinecarboxamide sustained by charge-assisted and conventional hydrogen bonds. J Struct Chem 46 (Suppl 1), S96–S102 (2005). https://doi.org/10.1007/s10947-006-0158-2

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  • DOI: https://doi.org/10.1007/s10947-006-0158-2

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