Full-text resources of PSJD and other databases are now available in the new Library of Science.
Visit https://bibliotekanauki.pl

PL EN


Preferences help
enabled [disable] Abstract
Number of results

Journal

2005 | 3 | 4 | 585-591

Article title

QSPR study on pKa values of N-methoxy-polynitroaniline derivatives

Content

Title variants

Languages of publication

EN

Abstracts

EN
A QSPR study is presented for acidities of thirteen N-methoxy-polynitroaniline derivatives. Hammett σ values are known for meta and para substituents, and in the present study values are introduced for ortho-substituents in these N-methoxy-polynitroaniline derivatives. Hammett σ values for ortho-substituents in these N-methoxy-polynitroaniline derivatives were obtained by multiplying para values with 0.65.

Publisher

Journal

Year

Volume

3

Issue

4

Pages

585-591

Physical description

Dates

published
1 - 12 - 2005
online
1 - 12 - 2005

Contributors

  • Laboratory of Supramolecular Chemistry and Interphase Processes, Institute “I. G. Murgulescu” of Physical Chemistry of Roumanian Academy, Splaiul Independenlei 202, 060021, Bucharest, Roumania

References

  • [1] G.W. Wheland: Resonance in Organic Chemistry, Wiley, New York, 1955.
  • [2] I.D. Rae: “A proton magnetic resonance study of molecular overcrowding in N-alkyl-o-nitroanilines”, Austral. J. Chem., Vol. 18, (1965), pp. 1807–1810. http://dx.doi.org/10.1071/CH9651807[Crossref]
  • [3] E. Kolehmainen, K. Laihia, G. Stanciuc and A.T. Balaban: “Strong para-substituent effects on rotational 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 and R.I. Walter: “Factors affecting stability and equilibria of free radicals. XII. 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 and 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 and 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] N. Zarna, G. Stanciuc, T. Constantinescu, F. Chiraleu, H. Caldararu, A. Caragheorgheopol, M.T. Caproiu, M. Ionecu and A.T. Balaban: “Electronic structure and acido-basic properties of some N-alkoxy-polynitroanilines”, Roum. Chem. Quart. Rev., Vol. 2, (1994), pp. 67–81.
  • [8] T.J. Sumi, G. Stanciuc, S. Kasa and H. Joela: “Hyperfine coupling of N-alkoxy-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] N. Zarna, T. Constantinescu, G. Stanciuc, A. Caragheorgheopol, H. Caldararu, A.T. Balaban, K. Laihla and E. Kolehmainen: “Hydrophobic supramolecular complexes of various cations with 18-crown-6 as the ligand and N-methoxy-pinramide as the anion pair in a water/methylene chloride two-phase system: complexes with isn't in document-amino acids, their characteristics and conditions for formation”, Supramolecular Science, Vol. 2, (1995), pp. 37–40. http://dx.doi.org/10.1016/0968-5677(96)85638-0[Crossref]
  • [10] G. Stanciuc, N. Zarna, N. Spataru, T. Constantinescu, A. Caragheorgheopol, H. Caldararu and A.T. Balaban: “Factors affecting stability and equilibria of free radicals. Part XXII. Bond dissociation energy of N-alkoxypolynitroanilines”, Rev. Roum. Chim., Vol. 41, (1996), pp. 755–761.
  • [11] I.C. Covaci, T. Constantinescu, M.T. Caproiu, C. Draghici, P. Ionita, C. Luca, G. Stanciuc, M. Maganu and A.T. Balaban: “3,5-Dinitro-4-methoxyaminobenzioc acid and its derivatives”, Rev. Roum. Chim., Vol. 44, (1999), pp. 333–340.
  • [12] D.O. Popescu, Ionita, N. Zarna, I. Covaci, A. Stoica, A. Zarna, D. Nourescu, F. Spafiu, M.T. Caproiu, C. Luca, F. Badea, T. Constantinescu and 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.
  • [13] I.C. Covaci, T. Constantinescu, M.T. Caproiu, F. Dumitrascu, C. Luca and A.T. Balaban: “New N-methoxy-dinitro-aniline derivatives: Synthesis, structure and pKα values”, Rev. Roum. Chim., Vol. 44, (1999), pp. 531–537.
  • [14] I.C. Covaci, T. Constantinescu, M.T. Caproiu, C. Luca and A.T. Balaban: “Solid supramolecular complexes of potassium salts of N-methoxynitroaniline derivatives and Methoxyamino-3,5-dimitropyridine with 18-crown-6 ether”, Eur. J. Org. Chem., (2000), pp. 3569–3573.
  • [15] N. Zarna, G. Stanciuc, T. Constantinescu, A.T. Balaban, K. Laihla and E. Kolehmainen: “Hydrophobic supramolecular complexes of alkali cations with 18-crown-6 as ligand and N-methoxy-2,4,6-trinitroaniline as pair anion in a two-phase system”, Rev. Roum. Chim., Vol. 41, (1996), pp. 875–881.
  • [16] A.T. Balaban, N. Frangopol, N. Negoita, P.T. Frangopol and M. Paraschiv: “Factors affecting stability and equilibria of free radicals. V. Synthesis and spectra of polynitrophenyl-alkoxy-amines”, Rev. Roum. Chim., Vol. 14, (1969), pp. 941–945.
  • [17] T. Constantinescu, M.T. Caproiu, N. Zarna, H. Caldararu, G. Stanciuc, M. Radu, V. Badescu and A.T. Balaban: “Reaction of 2,2-diphenyl-1-picrylhydrazyl (DPPH) with N-alkoxy di-and trinitroanilines”, New J. Chem., Vol. 41, (1997), pp. 575–579.
  • [18] H.H. Jaffé: “A reexamination of the Hammett equation”, Chem. Rev., Vol. 53, (1953), pp. 191–261. http://dx.doi.org/10.1021/cr60165a003[Crossref]
  • [19] P.R. Wells: “Linear free energy relationships”, Chem. Rev., Vol. 62, (1962), pp. 171–219.
  • [20] L.P. Hammett: “The effect of structure on the reaction of organic compounds. Benzene derivatives”, J. Am. Chem. Soc., Vol. 59, (1937), pp. 96–103. http://dx.doi.org/10.1021/ja01280a022[Crossref]
  • [21] K.B. Wiberg: “Substituent Effects on the Acidity of Weak Acids. 2. Calculated Gas-Phase Acidities of Substituted Benzoic Acids”, J. Org. Chem., Vol. 67, (2002), pp. 4787–4794. http://dx.doi.org/10.1021/jo020100i[Crossref]
  • [22] K.B. Wiberg: “Substituent Effects on the Acidity of Weak Acids. 1. Bicyclo(2.2.2.)octane-1-carboxylic Acids and Bicyclo(1.1.1)pentane-1-carboxylic Acids”, J. Org. Chem., Vol. 67, (2002), pp. 1613–1617. http://dx.doi.org/10.1021/jo011051x[Crossref]
  • [23] C. Hansch and A. Leo: Substituent Constants for Correlation Analysis in Chemistry and Biology, Wiley-Interscience, New York, 1979.
  • [24] C. Hansch, A. Leo and R.W. Taft: “A Survey of Hammett Substituent Constants and Resonance and Field Parameters”, Chem. Rev., Vol. 91, (1991) pp. 165–195. http://dx.doi.org/10.1021/cr00002a004[Crossref]
  • [25] A. Pross, L. Radom and R.W. Taft: “Theoretical approach to substituent effects. phenols and phenoxide ions”, J. Org. Chem., Vol. 45, (1980), pp. 818–826. http://dx.doi.org/10.1021/jo01293a012[Crossref]
  • [26] R.D. Topsom: “Discussion of theory and experiment”, Prog. Phys. Org. Chem., Vol. 16, (1987), pp. 85–124.
  • [27] M. Charton: “The application of the Hammett equation to ortho-substituted benzene reaction series”, Can. J. Chem., Vol. 38, (1960), pp. 2493–2499. http://dx.doi.org/10.1139/v60-338[Crossref]
  • [28] V. Balish and M. Uma: “Steric enhancement of resonance”, Tetrahedron Lett., Vol. 25, (1960), pp. 21–25. http://dx.doi.org/10.1016/S0040-4039(01)99388-8[Crossref]
  • [29] M.J. Kamlet: “Spectral effects of hydrogen-bonding in substituted anilines”, Israel J. Chem., Vol. 1, (1963), pp. 428–429. [Crossref]

Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_BF02475189
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.