Czasopismo
Tytuł artykułu
Autorzy
Warianty tytułu
Języki publikacji
Abstrakty
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
Czasopismo
Rocznik
Tom
Numer
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
autor
- Roumanian Academy, Institute “C. D. Nenitzescu” of Organic Chemistry, Splaiul Independentei 202B, 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
autor
- Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408, Bucharest, Roumania
autor
Bibliografia
- [1] I.C. Covaci, T. Constantinescu, M.T. Caproiu, C. Draghici, P. Ionita, C. Luca, G. Stanciuc, M. Maganu, A.T. Balaban: “3,5-Dinitro-4-methoxyaminobenzoic acid and its derivatives”, Rev. Roum. Chim., Vol. 44, (1999), pp. 333–340.
- [2] I. Covaci, T. Constantinescu, M.T. Caproiu, F. Dumitrascu, C. Luca, A. T. Balaban: “New N-methoxy-dinitro-aniline derivatives: synthesis, structure and pKa values”, Rev. Roum. Chim, Vol. 44, (1999), pp. 531–537.
- [3] E. Kolehmainen, K. Laihia, G. Stanciuc, A.T. Balaban: “Strong para-substituent effects on rorational barriers in N-alkoxy-4-R-2,6-dinitrobenzenamines. Dynamic 1H-NMR study”, Rev. Roum. Chim., Vol. 44, (1999), pp. 475–478.
- [4] G. Stanciuc, M.T. Caproiu, A. Caragheorgheopol, H. Caldararu, A.T. Balaban, R.I. Walter: “Factors affecting stability and equilibria of free radicals. XIII. N-Alkoxypicrylamines and ESR spectra of the corresponding capto-dative persistent aminyls”, J. Magn. Reson., Vol. 75, (1987), pp. 63–72.
- [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.
- [7] T.J. Sumi, G. Stanciuc, A.T. Balaban, H. Joela: “EPR and multiple electron resonance spectroscopic indication of para-nitration of aminyl radicals”, Magn. Reson. Chem., Vol. 34, (1996), pp. 197–206. http://dx.doi.org/10.1002/(SICI)1097-458X(199603)34:3<197::AID-OMR872>3.0.CO;2-A[Crossref]
- [8] T.J. Sumi, G. Stanciuc, S. Kasa, H. Joela: “Hyperfine coupling of N-polynitrophenylaminyl radicals determined by ENDOR and triple resonance spectroscopy”, Magn. Reson. Chem., Vol. 33 (1995), pp. 511–517. http://dx.doi.org/10.1002/mrc.1260330704[Crossref]
- [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.
- [10] I.C. Covaci, T. Constantinescu, M.T. Caproiu, H. Caldararu, P. Ionita, A.T. Balaban: “New congeners of 1-picryl-2-phenyl-2-(para-picramidophenyl)-diazenium betaine whose picramido groups are replaced by 4-cyano-2,6-dinitrophenyl analogs”, Polish J. Chem., Vol. 75, (2001), pp. 1427–1440.
- [11] G. Stanciuc and A.T. Balaban: “O-Alkoxy-N-arylhydroxylamines N-alkoxy-2,4,6-tri-and-2,6-dinitroanilines”, Org. Prep. Proc. Internat., Vol. 16, (1984), pp. 401–405. http://dx.doi.org/10.1080/00304948409458668[Crossref]
- [12] H. Mikola and E. Hanninen: “Introduction of aliphatic amino and hydroxy groups to keto steroids using O-substituted hydroxylamines”, Bioconj. Chem., Vol. 3, (1992), pp. 182–186. http://dx.doi.org/10.1021/bc00014a014[Crossref]
- [13] C. Reichardt: Solvents and Solvent Effects in Organic Chemistry, 2nd Ed., VCH Publ., Weinheim, 1988.
- [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]
- [17] T. Cserhati: “Relationship between the physicochemical parameters of 3,5-dinitrobenzoic acid esters and their retention behaviour on beta-cyclodextrin polymer support”, Anal. Chim. Acta, Vol. 292, (1994), pp. 17–22. http://dx.doi.org/10.1016/0003-2670(94)00035-2[Crossref]
- [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.
- [19] C. Hansch and A. Leo: Substituent Constants for Correlation Analysis in Chemistry and Biology, Wiley, New York, 1979.
- [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]
- [24] R.W. Baldock, P. Hudson, A.R. Katritzky, F. Soti: “Merostabilization. New principle governing the stability of organic free radicals”, Heterocycles, Vol. 1, (1973), pp. 67–71. http://dx.doi.org/10.3987/R-1973-01-0067[Crossref]
- [25] H.G. Viehe, Z. Janousek, R. Merenyi, L. Stella: “The captodative effect”, Acc. Chem. Res., Vol. 18, (1985), pp. 148–154. http://dx.doi.org/10.1021/ar00113a004[Crossref]
- [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