Abstract
Aromaticity/aromatic belongs to one of the most useful and popular terms in organic chemistry and related fields. However, aromaticity is not an unambiguous term; therefore, its definition is enumerative. The criteria are based on energy (increased stability), molecular geometry (very low bond lengths alternation), magnetism (induction of the diatropic ring current by external magnetic field) and reactivity (tendency to maintain π-electron structure in chemical reactions). The energetic criterion is based on resonance energy and aromatic stabilization energy, whereas harmonic oscillator model of aromaticity—on molecular geometry. Magnetism-based criteria are illustrated by local indicators (for individual rings): nucleus independent chemical shifts and proton nuclear magnetic resonance chemical shifts as well as the global aromaticity index—exaltation of the magnetic susceptibility. For selected homo- and hetero-cyclic compounds, illustrative data are presented in tables, which allow the comparison of the above-mentioned indices. Finally, examples of agreements or disagreements between these various aromaticity indices are presented for few representative cases.Electronic supplementary materialThe online version of this article (doi:10.1007/s40828-015-0012-2) contains supplementary material, which is available to authorized users.
Highlights
Aromaticity is a very frequently used term in chemistry and in related fields
The energetic criterion is based on resonance energy and aromatic stabilization energy, whereas harmonic oscillator model of aromaticity—on molecular geometry
Magnetism-based criteria are illustrated by local indicators: nucleus independent chemical shifts and proton nuclear magnetic resonance chemical shifts as well as the global aromaticity index—exaltation of the magnetic susceptibility
Summary
Aromaticity is a very frequently used term in chemistry and in related fields. Every day *30 papers appear in which the terms ‘aromatic/aromaticity’ are used in either their titles or abstracts or the keywords [1]. Numerous organic compounds are either aromatic or contain aromatic fragments. The definition of aromaticity is enumerative in nature, i.e. it is described by a collection of physicochemical properties determining specific features of cyclic or polycyclic p-electron molecules [2,3,4].
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