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2003 | 1 | 1 | 53-64
Tytuł artykułu

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

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
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.
Słowa kluczowe
Wydawca

Czasopismo
Rocznik
Tom
1
Numer
1
Strony
53-64
Opis fizyczny
Daty
wydano
2003-03-01
online
2003-03-01
Twórcy
autor
  • Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania
autor
  • Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania
  • Roumanian Academy, Institute “C. D. Nenitzescu” of Organic Chemistry, Splaiul Independentei 202B, 77408, Bucharest, Roumania
  • Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania
  • Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania
Bibliografia
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  • [5] G. Stanciuc, M.T. Caproiu, A. Caragheorgheopol, H. Caldararu, T. Constantinescu, A.T. Balaban: “Factors affecting stability and equilibria of free radicals. XVI. Preparation and EPR spectra of capto-dative N-alkoxy-dinitrophenyl-aminyls”, Rev. Roum. Chim., Vol. 34, (1989), pp. 1895–1905.
  • [6] G. Stanciuc, M.T. Caproiu, A. Caragheorgheopol, H. Caldararu, T. Constantinescu, A.T. Balaban: “Factors affecting stability and equilibria of free radicals. XV. EPR evidence of formation of N-alkoxypicramides on oxidation of N-alkoxy-dinitroanilines. Electronic structure of aminyl radicals”, Z. Naturforsch., Vol. 44b, (1989), pp. 1459–1463.
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  • [9] T. Constantinescu, M.T. Caproiu, N. Zarna, A. Caragheorgheopol, H. Caldararu, G. Stanciuc, M. Radu, V. Badescu, A.T. Balaban: “Reaction of 2,2-diphenyl-1-picrylhydrazyl (DPPH) with N-alkoxy di and trinitroanilines”, New. J. Chem., Vol. 21, (1997), pp. 575–579.
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  • [14] N. Zarna, G. Stanciuc, T. Constantinescu, F. Chiraleu, H. Caldararu, A. Caragheorgheopol, M.T. Caproiu, M. Ionescu, A.T. Balaban: “Electronic structure and acido-basic properties of some N-alkoxy-polynitroanilines”, Roum. Chem. Quart. Rev., Vol. 2, (1994), pp. 67–81.
  • [15] D.O. Popescu, P. Ionita, N. Zarna, I. Covaci, A. Stoica, A. Zarna, D. Nourescu, F. Spahiu, M.T. Caproiu, C. Luca, F. Badea, T. Constantinescu, A. T. Balaban: “Hydrazyl and aminyl analogs, liquid membranes and stationary phases for gas chromatography”, Roum. Chem. Quart. Rev., Vol. 6, (1998), pp. 271–282.
  • [16] N. Zarna, T. Constantinescu, H. Caldararu, A. Caragheorgheopol, G. Stanciuc, A.T. Balaban, K. Laihia, E. Kolehmainen: “Hydrophobic supramolecular complexes of various cations with 18-crown-6 as the ligand and N-methoxy-picramide as the anion pair in a water/methylene chloride two-phase system: complexes with alpha-amino acids, their characteristics and conditions for formation”, Supramol. Sci., Vol. 2, (1995), pp. 37–41. http://dx.doi.org/10.1016/0968-5677(96)85638-0[Crossref]
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  • [18] G. Ionita, T. Constantinescu, P. Ionita: “Normal and reversed phase TLC of some hydrazine derivatives”, J. Planar Chromatogr., Vol. 11, (1998), pp. 141–144.
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  • [20] A.J. Leo: “Calculating log Poct from structures”, Chem. Rev., Vol. 93, (1993), pp. 1281–1306. http://dx.doi.org/10.1021/cr00020a001[Crossref]
  • [21] M.J.S. Dewar: “A molecular orbital theory of organic compounds. 4. Free radicals”, J. Am. Chem. Soc., Vol. 74, (1952), pp. 3353–3354. http://dx.doi.org/10.1021/ja01133a041[Crossref]
  • [22] A.T. Balaban: “Stable nitrogen free radicals”, Rev. Roum. Chim., Vol. 16, (1971), pp. 725–37.
  • [23] A.T. Balaban, PT. Frangopol, M. Frangopol, N. Negoita: “Stability and equilibria of free radicals. III. Preparation of stable, sterically shielded, diarylnitrogen radicals with donor and acceptor aryl groups in the same molecule”, Tetrahedron, Vol. 23, (1967), pp. 4661–4676. http://dx.doi.org/10.1016/S0040-4020(01)92564-5[Crossref]
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  • [26] H.G. Viehe, Z. Janousek, R. Merenyi, Eds., Substituent Effects in Radical Chemistry, NATO Series C (Mathematical and Physical Sciences), Vol. 189, Reidel Publ., Dordrecht, 1986.
  • [27] H.G. Viehe, R. Merenyi, L. Stella, Z. Janousek: “Captodative substitutions”, Angew. Chem., Vol. 91, (1979), pp. 651–652.
  • [28] D.K.W. Dixon, R.H. Weiss, W.A. Nelson: “The 1,4,2,3-dioxadiazine ring system”, Tetrahedron Lett., Vol. 24, (1983), pp. 4393–4396. http://dx.doi.org/10.1016/S0040-4039(00)85906-7[Crossref]
  • [29] P. Ionita, M.T. Caproiu, A.T. Balaban: “New sulfonyl derivatives of 2,2-diphenyl-1-picrylhydrazyl and their supramolecular complexes with crown ethers or kryptands”, Rev. Roum. Chim., Vol. 45, (2000), pp. 935–941.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02479257
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