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

100%

Covaci I., Ionita P., Caproiu M., Socoteanu R., Constantinescu T., Balaban A.

Open Chemistry

2003

vol. 1

issue 1

53-64

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.

A theoretical study of the limits of the acidity of carbon acids in phase transfer catalysis in water and in liquid ammonia

100%

Alkorta I., Elguero J., Gallo R.

Open Chemistry

2013

vol. 11

issue 11

1711-1722

The acidities of a large number of carbon acids have been theoretically calculated for the gas-phase and for DMSO solution. The gas-phase values, both ΔH and ΔG, are very well correlated with the available experimental data. From the calculated ΔG values in DMSO and the pKas in the same solvent, a homogeneous set of pK a (DMSO) values was devised that was used to generate pK a (water). These last pK as were used to establish the limits of the acidity of carbon acids for reactions under PTC conditions both alkylations and H/D exchange. A step further led to the pK as in liquid ammonia and from them to the virtual use of PTC using liquid ammonia instead of water. [...]

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2 Open Chemistry

1 2013

1 2003

1 Alkorta I.

1 Balaban A.

1 Caproiu M.

1 Constantinescu T.

1 Covaci I.

1 Elguero J.

1 Gallo R.

1 Ionita P.

1 Socoteanu R.

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

A theoretical study of the limits of the acidity of carbon acids in phase transfer catalysis in water and in liquid ammonia