Nitration of naphthalene and remarks on the mechanism of electrophilic aromatic nitration

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Nitration of naphthalene and remarks on the mechanism of electrophilic aromatic nitration.

Naphthalene was nitrated with a variety of nitrating agents. Comparison of data with Perrin's electrochemical nitration [Perrin, C. L. (1977) J. Am. Chem. Soc. 99, 5516-5518] shows that nitration of naphthalene gives an alpha-nitronaphthalene to beta-nitronaphthalene ratio that varies between 9 and 29 and is thus not constant. Perrin's data, therefore, are considered to be inconclusive evidence...

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Mechanism and regioselectivity of electrophilic aromatic nitration in solution: the validity of the transition state approach

The potential energy surfaces in gas phase and in aqueous solution for the nitration of benzene, chlorobenzene, and phenol have been elucidated with density functional theory at the M06-2X/6-311G(d,p) level combined with the polarizable continuum solvent model (PCM). Three reaction intermediates have been identified along both surfaces: the unoriented π-complex (I), the oriented reaction comple...

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Electrophilic aromatic nitrosation and nitration are among the most important electron transfer (ET) reactions. According to the electron transfer theory, an ET process can be described with two electron-localized diabatic states, and the electronic coupling between these two states, together with the organization energy and reaction energy, determine the ET efficiency. A proper definition of t...

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ژورنال

عنوان ژورنال: Proceedings of the National Academy of Sciences

سال: 1981

ISSN: 0027-8424,1091-6490

DOI: 10.1073/pnas.78.6.3298