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Open Chemistry

formerly Central European Journal of Chemistry


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Volume 1, Issue 1

Issues

Volume 13 (2015)

1,3-bis(2,4,6-trinitrophenylaminooxy)propane and its 4-cyano-2,6-dinitrophenyl congener: Synthesis and properties

Irina Covaci
  • Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania
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/ Petre Ionita
  • Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania
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/ Miron Caproiu
  • Roumanian Academy, Institute “C. D. Nenitzescu” of Organic Chemistry, Splaiul Independentei 202B, 77408, Bucharest, Roumania
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/ Radu Socoteanu
  • Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania
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/ Titus Constantinescu
  • Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania
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/ Alexandru Balaban
  • Department of Organic Chemistry, University “Polytechnica”, Faculty of Industrial Chemistry, Bucharest, Roumania
  • Texas A&M University at Galveston, 77553-1675, Galveston, TX, USA
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Published Online: 2003-03-01 | DOI: https://doi.org/10.2478/BF02479257

Abstract

Starting from N-hydroxyphthalimide (5) and 1,3-dibromopropane (6) we obtained 1,3-bis(phthalimidooxy)propane (7) which led to 1,3-bis(aminooxy)propane dihydrochloride (8). From its reaction with picryl chloride or 4-cyano-2,6-dinitrochlorobenzene, the two title compounds (4b, 4a) were obtained.

1H-NMR and 13C-NMR spectra are presented. For comparison with the analogous N-methoxy-2,6-dinitro-4-R-anilines 1a, 1b (R=CN or R=NO2), wer report the hydrophobic characteristics (by RPTLC), electronic spectra for the neutral compounds and their anions, pKa values, and the behavior towards oxidizers (DPPH, PbO2, Pb(CH3COO)4, KMnO4 and Ag2O); DPPH converts compounds 1a, 1b and 4a, 4b into betainic structures 2a, 2b respectively.

Keywords: N-alkoxyaryl derivatives; RPTLC; pKa; NMR; oxidation

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About the article

Published Online: 2003-03-01

Published in Print: 2003-03-01


Citation Information: Open Chemistry, Volume 1, Issue 1, Pages 53–64, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/BF02479257.

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© 2003 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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