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Aromaticity in Heterocyclic Compounds

  • Book
  • © 2009

Overview

Editors:
  1. Tadeusz M. Krygowski

    1. Department of Chemistry, University of Warsaw, Warszawa, Poland

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    You can also search for this editor in PubMed   Google Scholar

  2. Michał K. Cyrański

    1. Department of Chemistry, University of Warsaw, Warszawa, Poland

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    You can also search for this editor in PubMed   Google Scholar

  • Heterocyclic chemistry is the biggest branch of chemistry covering two-third of the chemical literature

  • Series covers hot topics of frontier research summarized by reputed scientists in the field

  • Our review series is topic related

  • Online version available on SpringerLink.com

  • Includes supplementary material: sn.pub/extras

Part of the book series: Topics in Heterocyclic Chemistry (TOPICS, volume 19)

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Table of contents (7 chapters)

  1. Front Matter

    Pages i-xiii
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  2. Experimental Thermochemistry of Heterocycles and Their Aromaticity: A Study of Nitrogen, Oxygen, and Sulfur Derivatives of Indane and Indene

    • M. Agostinha R. Matos, Joel F. Liebman
    Pages 1-26

  3. Aromatic Phosphorus Heterocycles

    • L. Nyulászi, Z. Benkő
    Pages 27-81

  4. Aromaticity and Tautomerism in Porphyrins and Porphyrinoids

    • M Stępień, L. Latos-Grażyński
    Pages 83-153

  5. How Aromaticity Affects the Chemical and Physicochemical Properties of Heterocycles: A Computational Approach

    • I. Alkorta, J. Elguero
    Pages 155-202

  6. Aromaticity of Six-Membered Rings with One Heteroatom

    • A.T. Balaban
    Pages 204-246

  7. Chemistry of Hetero Analogs of Pentalene Dianion

    • A. Krutošíková, T. Gracza
    Pages 247-285

  8. New Trends in Chemistry and Application of Aromatic and Related Selenaheterocycles

    • J. Młochowski, M. Giurg
    Pages 288-340

  9. Back Matter

    Pages 341-344
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Keywords

About this book

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].

Editors and Affiliations

  • Department of Chemistry, University of Warsaw, Warszawa, Poland

    Tadeusz M. Krygowski, Michał K. Cyrański

Bibliographic Information

  • Book Title: Aromaticity in Heterocyclic Compounds

  • Editors: Tadeusz M. Krygowski, Michał K. Cyrański

  • Series Title: Topics in Heterocyclic Chemistry

  • DOI: https://doi.org/10.1007/978-3-540-68343-8

  • Publisher: Springer Berlin, Heidelberg

  • eBook Packages: Chemistry and Materials Science, Chemistry and Material Science (R0)

  • Copyright Information: Springer-Verlag Berlin Heidelberg 2009

  • Hardcover ISBN: 978-3-540-68329-2Published: 30 January 2009

  • Softcover ISBN: 978-3-642-08793-6Published: 20 November 2010

  • eBook ISBN: 978-3-540-68343-8Published: 16 December 2008

  • Series ISSN: 1861-9282

  • Series E-ISSN: 1861-9290

  • Edition Number: 1

  • Number of Pages: XIII, 344

  • Number of Illustrations: 80 b/w illustrations, 8 illustrations in colour

  • Topics: Organic Chemistry

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