Nitrosobenzene Library: A Model for Studying Selectivity in the Solid State Nitroso-Azodioxide Dimerization

Šimunić-Mežnarić, Vesna and Meštrović, Ernest and Tomišić, Vladislav and Žgela, Marijana and Vikić-Topić, Dražen and Čičak, Helena and Novak, Predrag and Vančik, Hrvoj (2005) Nitrosobenzene Library: A Model for Studying Selectivity in the Solid State Nitroso-Azodioxide Dimerization. Croatica Chemica Acta, 78 (4). pp. 511-518. ISSN 0011-1643

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Cross-linking of nitroso benzenes to heterodimers (azodioxides), in the case when they are not sterically crowded with large groups in ortho-position, was studied by NMR, UV-VIS, and Raman spectroscopy as well as by powder X-ray crystallography. Dimerization of nitroso compounds to azodioxides can, in principle, be used for the construction of novel supramolecular structures. As a preliminary investigation, the selectivity of nitrosobenzenes to form dimers in the solid state was studied. Observations by NMR and vibrational spectroscopy show that selectivity for cross-linking is quite different in the solid state from that in solution. This is explained by a considerable influence of packing factors in the former. Selectivities for cross-linking in the solid state in a complex chemical library of monomers were formulated and measured using simple spectroscopic and diffraction methods. For every member of such a nitrosobenzene chemical library it is possible to measure and, using the Tanimoto similarity coefficients, calculate two selectivity parameters, chemical selectivity and packing selectivity. While packing selectivity is correlated with total dipole moments of nitroso monomer molecules, chemical selectivity is in correlation with the x-component of the molecular dipole, i.e., the axis that is nearly collinear with the C-N bond in nitroso group. The method developed in this work could, in principle, be proposed for more general use in investigations of similar chemical libraries with binary combined components.

Item Type: Article
Keywords: solid state reactivity; solid state selectivity; nitroso compounds; chemical library
Date: 2005
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Faculty of Science > Department of Chemistry
Publisher: Hrvatsko kemijsko društvo
Related URLs:
Depositing User: mag. bibl. Ana Šafran
Date Deposited: 16 May 2014 07:50
Last Modified: 16 May 2014 07:50

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