Abstract
This research focuses on the X-ray structure of 4,6-dichloro-5-nitrobenzofuroxan 1 and of some of its amino derivatives (4a, 4e, 4g, and 4l) and on DFT calculations concerning the nucleophilic reactivity of 1. We have found that by changing the solvent used for crystallization, it is possible to obtain 4,6-dichloro-5-nitrobenzofuroxan (1) in different polymorphic structures. Moreover, the different torsional angles observed for the nitro group in 1 and in its amino derivatives (4a, 4e, 4g, and 4l) are strictly dependent on the steric hindrance of the substituent at C-4. DFT calculations on the course of the nucleophilic substitution confirm the role of the condensed furoxan ring in altering the aromaticity of the carbocyclic frame, while chlorine atoms strongly influence the dihedral angle and the rotational barrier of the nitro group. These results corroborate previous observations based on experimental kinetic data and give a deep picture of the reaction with amines, which proceeds via a “non-aromatic” nucleophilic substitution.
Highlights
Introduction iationsIn line with our interest in the study of the reactivity/activity of heterocyclic compounds, we thoroughly investigated the chemical/biological behavior of several classes of heterocycles containing nitrogen, oxygen, and sulphur atoms
Looking at 4,6-dichloro-5-nitrobenzofuroxan (1) its structure was confirmed by XLooking
Starting from some kinetic results collected studying the reactivity of 4,6-dichloro-5ntrobenzofuroxan (1) with several nitrogen nucleophiles [7], we enlarged our interest to the study of the X-ray structure of 1 and of some of its amino derivatives
Summary
In line with our interest in the study of the reactivity/activity of heterocyclic compounds, we thoroughly investigated the chemical/biological behavior of several classes of heterocycles containing nitrogen, oxygen, and sulphur atoms. Considering that in the last few decades, the interest of chemists has been deeply focused on the pharmaceutical/pharmacological activities of several heterocyclic compounds [13,14,15], we evaluated some of their cardiovascular [16], antitumor [17], or anti-MDR1 [18] effects. The study of biologically active compounds is one of the most interesting and rapidly developing branches of organic chemistry.
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