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Aromaticity in Heterocyclic Compounds (Hardcover, 2009 ed.)
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Aromaticity in Heterocyclic Compounds (Hardcover, 2009 ed.)
Series: Topics in Heterocyclic Chemistry, 19
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Total price: R8,149
Discovery Miles: 81 490
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Aromaticity is a notion that appeared in the mid-nineteenth century
to differentiate between unsaturated hydrocarbons and formally
unsaturated benzene [1-3]. At the end of the nineteenth century it
seemed that cyclicity was a necessary condition for differentiation
between the two, but at the beginning of the twentieth century it
turned out that the above assumption was not correct because
cyclooctatetraene exhibited typical properties known for polyenes
[4]. The essential property of b- zene-like compounds, often
identified with aromatic compounds, was low react- ity. Hence
thermodynamic stability was defined as resonance energy [5, 6] and
was the first quantitative measure of aromaticity. Many theoretical
approaches were proposed later to estimate this quantity, and now
the criterion is often considered to be the most fundamental [7].
Almost at the same time, magnetic susceptibility was used to
describe aromaticity [8, 9]. Consequently, many concepts based on
mag- tism were developed, probably the most effective in assessment
of aromaticity being nucleus independent chemical shift (NICS) [10]
or Fowler's maps of ring currents [11]. The criterion served
Schleyer as a basis for a definition of aromat- ity: "Compounds
which exhibit significantly exalted diamagnetic susceptibility are
aromatic. Cyclic delocalisation may also result in bond length
equalization, abn- mal chemical shifts and magnetic anisotropies,
as well as chemical and physical properties which reflect energetic
stabilisation"[12].
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