PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Czasopismo
2010 | 8 | 4 | 789-796
Tytuł artykułu

New N-aryloxy-phthalimide derivatives. Synthesis, physico-chemical properties, and QSPR studies

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Starting from N-hydroxyphthalimide 1 and the reactive fluoro- or chloro-nitroaryl derivatives 2, 3 and 4a-e (2-chloro-3,5-dinitropyridine; 3, NBD-chloride; 4a, 1-fluoro-2,4-dinitrobenzene; 4b, picryl chloride; 4c, 4-chloro-3,5-dinitrobenzotrifluoride; 4d, 2-chloro-3,5- dinitrobenzotrifluoride; 4e, 4-chloro-3,5-dinitrobenzoic acid) the corresponding N-(2-nitroaryloxy)-phthalimide derivatives 5a-e, or 6 and 7 were obtained and characterized by IR, UV-Vis 1H-NMR and 13C-NMR spectroscopy. The TLC behavior and the hydrophobicity of these derivatives have been experimentally evaluated by RM0 parameters (using RP-TLC). The experimental RM0 parameters were compared with the calculated partition coefficient, log P. A QSPR study was also performed to establish possible correlations between the structure and physical properties (λmax and RM0) of compounds 5a-e, 6, and 7. [...]
Słowa kluczowe
Wydawca

Czasopismo
Rocznik
Tom
8
Numer
4
Strony
789-796
Opis fizyczny
Daty
wydano
2010-08-01
online
2010-06-17
Twórcy
  • Institute of Physical Chemistry, 202 Splaiul Independentei, Bucharest, 060021, Romania
autor
  • Organic Chemistry Department, University Politehnica Bucharest, Bucharest, 011061, Romania
  • Center of Organic Chemistry, 202 Splaiul Independentei, Bucharest, 060023, Romania
  • Institute of Physical Chemistry, 202 Splaiul Independentei, Bucharest, 060021, Romania
autor
  • Center of Organic Chemistry, 202 Splaiul Independentei, Bucharest, 060023, Romania
autor
  • Institute of Physical Chemistry, 202 Splaiul Independentei, Bucharest, 060021, Romania
Bibliografia
  • [1] A. Karakurt, S. Dalkara, M. Ozalp, S. Ozbey, E. Kendi, J. P. Stables, Eur. J. Med. Chem. 36, 421 (2001) http://dx.doi.org/10.1016/S0223-5234(01)01223-5[Crossref]
  • [2] L. Cohn, Liebigs Ann. Chem. 205, 295 (1880) http://dx.doi.org/10.1002/jlac.18802050304[Crossref]
  • [3] A.L. Green, G.L. Sainpbury, B. Saville, M.J. Stansfield, J. Chem. Soc. 1583 (1958) [Crossref]
  • [4] S. Coseri, Catal. Rev. 51, 218 (2009) http://dx.doi.org/10.1080/01614940902743841[Crossref]
  • [5] S. Coseri, G.D. Mendenhall, K.U. Ingold, J. Org. Chem. 70, 4629 (2005) http://dx.doi.org/10.1021/jo0504060[Crossref]
  • [6] S. Coseri, Mini-Rev. Org. Chem. 5, 222 (2008) http://dx.doi.org/10.2174/157019308785161675[Crossref]
  • [7] S. Coseri, Eur. J. Org. Chem. 1725 (2007) [Crossref]
  • [8] Y. Ishii, T. Iwaham, S. Sakaguchi, K. Nakayama, M. Takeno, Y. Nishiyama, J. Org. Chem. 61, 4520 (1996) http://dx.doi.org/10.1021/jo951970l[Crossref]
  • [9] Y. Yoshino, Y. Hayashi, T. Iwahama, S. Sakaguchi, Y. Ishii, J. Org. Chem. 62, 6810 (1997) http://dx.doi.org/10.1021/jo9708147[Crossref]
  • [10] B.B. Wentzel, M.P.J. Donners, P.L. Alsters, M.C. Feiters, R.J.M. Nolte, Tetrahedron 56, 7797 (2000) http://dx.doi.org/10.1016/S0040-4020(00)00679-7[Crossref]
  • [11] T. Iwahama, Y. Yosshima, T. Keitoku, S. Sakaguchi, Y. Ishii, J. Org. Chem. 65, 6502 (2000) http://dx.doi.org/10.1021/jo000760s[Crossref]
  • [12] F. Minisci, C. Punta, F. Recupero, F. Fontana, G.F. Pedulli, Chem. Commun. 688 (2002) [Crossref]
  • [13] A. Cecchetto, F. Minisci, F. Recupero, F. Fontana, G.F. Pedulli, Tetrahedron Lett. 43, 3605 (2002) http://dx.doi.org/10.1016/S0040-4039(02)00474-4[Crossref]
  • [14] F. Minisci, C. Punta, F. Recupero, F. Fontana, G.F. Pedulli, J. Org. Chem. 67, 2671 (2002) http://dx.doi.org/10.1021/jo016398e[Crossref]
  • [15] A. Rougny, M. Daudon, Bull. Soc. Chim. Fr. 5, 833 (1976)
  • [16] L. Bauer, K.S. Suresh, J. Org. Chem. 28, 1604 (1963) http://dx.doi.org/10.1021/jo01041a042[Crossref]
  • [17] H. Mikola, E. Hänninen, Bioconjugate Chem. 3, 182 (1992) http://dx.doi.org/10.1021/bc00014a014[Crossref]
  • [18] I.C. Covaci, P. Ionita, M.T. Caproiu, R. Socoteanu, T. Constantinescu, A.T. Balaban, Cent. Eur. J. Chem. 1, 57 (2003) http://dx.doi.org/10.2478/BF02479257[Crossref]
  • [19] C. Legault, A.B. Charette, J. Org. Chem. 68, 7119 (2003) http://dx.doi.org/10.1021/jo034456l[Crossref]
  • [20] P. Ionita, M.T. Caproiu, A.T. Balaban, Rev. Roum. Chim. 45, 935 (2000)
  • [21] MOPAC 2007, J.J.P. Stewart, Stewart Computational Chemistry, Colorado Springs, USA, http://openmopac.net
  • [22] J.J.P. Stewart, J. Computational Chemistry 10, 221(1989) http://dx.doi.org/10.1002/jcc.540100209[Crossref]
  • [23] M.A. Thompson, ArgusLab 4.0.1 (Planaria Software LLC, Seattle, WA, 2004) http://www.arguslab.com
  • [24] N.L. Allinger, J. Am. Chem. Soc. 99, 8127 (1977) http://dx.doi.org/10.1021/ja00467a001[Crossref]
  • [25] M.J. S. Dewar, E.G. Zoebisch, E.F. Healy, J.J.P. Stewart, J. Am. Chem. Soc. 107, 3902 (1985) http://dx.doi.org/10.1021/ja00299a024[Crossref]
  • [26] J. Baker, J. Comp. Chem. 7, 385 (1986) http://dx.doi.org/10.1002/jcc.540070402[Crossref]
  • [27] A.A. Granovsky, Dept. of Chemistry, (Moscow State University (MSU), Russia, 2009) PCGames/Fireflyversion 7.1.G,http://classic.chem.msu.su/gran/gamess/index
  • [28] F. Terrier, Nucleophilic Aromatic Displacement (VCH, New York, 1991)
  • [29] J. Miller, Aromatic Nucleophilic Substitution (Elsevier, Amsterdam, 1968)
  • [30] S.-X. Wang, X.-W. Li, J.-T. Li, Ultrasonics Sonochemistry 15, 33 (2008) http://dx.doi.org/10.1016/j.ultsonch.2007.07.005[Crossref]
  • [31] HyperChem(TM) (Hypercube, Inc., Gainesville, Florida, USA, 2008)
  • [32] M. Bem, M. Vasilescu, M.T. Caproiu, A. Beteringhe, T. Constantinescu, M.D. Banciu, A.T. Balaban, Cent. Eur. J. Chem. 2, 237 (2004) http://dx.doi.org/10.2478/BF02482730[Crossref]
  • [33] E. Soczewinski, Anal. Chem. 41, 179 (1969) http://dx.doi.org/10.1021/ac60270a035[Crossref]
  • [34] E. Soczewinski, J. Chromatogr. 388, 91 (1987) http://dx.doi.org/10.1016/S0021-9673(01)94469-3[Crossref]
  • [35] G. Ionita, T. Constantinescu, P. Ionita, J. Planar Chromatogr. Modern TLC 11, 141 (1998)
  • [36] M. Bem, M.T. Caproiu, D. Stoicescu, T. Constantinescu, A.T. Balaban, Cent. Eur. J. Chem. 3, 260 (2003) http://dx.doi.org/10.2478/BF02476228[Crossref]
  • [37] C. Hansch, A. Leo, Substituent Constants for Correlation Analysis in Chemistry and Biology (Wiley, New York, 1979)
  • [38] M.S. Gordon, M.W. Schmidt, In: C.E. Dykstra, G. Frenking, K.S. Kim, G.E. Scuseria (Eds.), Theory and Applications of Computational Chemistry: the First Forty Years (Elsevier, Amsterdam, 2005) 1167 http://dx.doi.org/10.1016/B978-044451719-7/50084-6
  • [39] A.R. Katritzky, V.S. Lobanov, M. Karelson, CODESSA: A Reference Manual (Version 2.0) (Gainesville, Florida, 1994)
  • [40] A.R. Katritzky, S. Perumal, R. Petrukhin, E. Kleinpeter, J. Chem. Inf. Comp. Sci. 41, 56 (2001) [Crossref]
  • [41] L.B. Kier, J. Pharm. Sci. 69, 807 (1980) http://dx.doi.org/10.1002/jps.2600690717[Crossref]
  • [42] D. Bonchev, Information Theoretic Indices for Characterization of Chemical Structure (Wiley-Interscience, New York, 1983)
  • [43] K. Fukui, Theory of Orientation and Stereoselection (Springer-Verlag, Berlin, 1975)
  • [44] W. C. Griffin, J. Soc. Cosmetic Chemists 1, 311 (1949)
  • [45] W.C. Griffin, J. Soc. Cosmetic Chemists 5, 249 (1954)
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-010-0063-6
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.