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

• Authors: Irina Covaci , Petre Ionita , Miron Caproiu , Radu Socoteanu , Titus Constantinescu , Alexandru Balaban
• Languages of publication: EN

Abstracts

EN

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

EN

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

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2003
• Volume: 1
• Issue: 1
• Pages: 53-64

Dates

published

1 - 3 - 2003

online

1 - 3 - 2003

Contributors

author

Irina Covaci

• Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania

author

Petre Ionita

• Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania

author

Miron Caproiu

• Roumanian Academy, Institute “C. D. Nenitzescu” of Organic Chemistry, Splaiul Independentei 202B, 77408, Bucharest, Roumania

author

Radu Socoteanu

• Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania

author

Titus Constantinescu

• Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania

author

Alexandru Balaban

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Identifiers

DOI

10.2478/BF02479257