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Proton affinity of substituted naphthalenes

✍ Scribed by M. Eckert-Maksić; I. Antol; M. Klessinger; Z. B. Maksić

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
97 KB
Volume
12
Category
Article
ISSN
0894-3230

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✦ Synopsis

The absolute proton affinity (PA) of aromatic carbons of monosubstituted naphthalenes with CH 3 , OH, CHO, NO 2 and Cl substituents was calculated at the MP2(fc)/6-31G**//HF/6-31G* ZPVE(HF/6-31G*) level of theory. Increments corresponding to unsubstituted positions within the naphthalene skeleton were estimated. They can be used in estimating PAs of polysubstituted naphthalenes by using a simple additivity rule based on the independent substituent approximation (ISA). It is shown that increments are good indicators of the electrophilic substitution reactivity. The proton affinities of a large number of polysubstituted methylnaphthalenes was examined employing the additivity equation. It was found that the protonated forms, which exhibit the largest PAs, correspond to arenium ions observed by NMR spectroscopy in superacid media.

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