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Aromaticity of Six-Membered Rings with One Heteroatom

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Topics in Heterocyclic Chemistry

Part of the book series: Topics in Heterocyclic Chemistry

Abstract

Six-membered rings with one heteroatom are aromatic when there is a continuous conjugation involving six delocalized electrons. The main-group heteroatom from groups 16–13 of the periodic system can be (ordered approximately according to decreasing electronegativity): O+, S+, Se+, Te+, NR+, N+–O−, N, P, PR2, As, Sb, Bi, SiR, GeR, BR−, and GaR−. Among elements that give rise to aromatic metallabenzenes, so far most investigations have concentrated on Os, Ir, Pt, and Rh. Various qualitative and quantitative aspects of aromaticity are reviewed, such as chemical reactivity, molecular geometry, energetics, and magnetic features.

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Abbreviations

ANRORC:

Attack by nucleophile, ring opening, ring closure

DFT:

Density functional theory

DNA:

Deoxyribonucleic acid

EN:

Term in HOMA due to the bond length alternation

EWG:

Electron withdrawing group

GEO:

Term in HOMA due to the bond elongation

HOMA:

Harmonic oscillator model of aromaticity

HOSE:

Harmonic oscillator stabilization energy

IUPAC:

International Union of Pure and Applied Chemistry

NICS:

Nucleus independent chemical shift

NMR:

Nuclear magnetic resonance

NRT:

Natural resonance theory

RE:

Resonance energy

RNA:

Ribonucleic acid

Tbt:

Tris[bis(trimethylsilyl)methyl]phenyl

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    A. T. Balaban

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Balaban, A.T. (2008). Aromaticity of Six-Membered Rings with One Heteroatom. In: Topics in Heterocyclic Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2008_2

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