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pp 1-44 | Cite as

Aromaticity of Six-Membered Rings with One Heteroatom

  • A. T. Balaban
Chapter
Part of the Topics in Heterocyclic Chemistry book series

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.

Keywords

aromaticity arsabenzene boratabenzene germabenzene heterocycles metallabenzene phosphabenzene pyridine pyridinium pyrylium silabenzene thiopyrylium 

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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© Springer-Verlag 2008

Authors and Affiliations

  1. 1.Texas A&M University at GalvestonGalvestonUSA

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