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Über dieses Buch

Hellwinkel gives a short and general introduction to the systematic nomenclature of organic compounds. On the basis of carefully selected examples it offers simple and concise guidelines for the generation of systematic compound names as codified by the IUPAC rules. Besides the most common compound classes important special areas such as cyclophanes, carbohydrates, organometallic and isotopically modified compounds and stereochemical specifications are dealt with. In cases where there is not yet a finalised set of IUPAC rules, possibilities for logical and desirable extensions of existing rules are outlined. Likewise, deviations from Chemical Abstracts and Beilstein index names are noted, if significant. The German version (4th edition) is meanwhile a longseller.

Inhaltsverzeichnis

Frontmatter

Introduction

Abstract
The downright indifference or even aversion of many chemists to appelation problems of their science is to some degree understandable since there are simply too many divergent and inhomogeneous nomenclature systems to choose from. Moreover, the same naming principles are frequently applied quite differently by different chemical journals, textbooks and handbooks. Meanwhile, however, consensus has been reached to use, wherever possible, an internationally binding uniform nomenclature system that nevertheless tolerates certain alternatives. It has therefore become necessary for every chemist — whether student or professionally active — to acquire at least an elementary working knowledge of this system. This is all the more urgent since indexing by the globally active Chemical Abstracts Service (Chem. Abstr.) and by Beilsteins Handbook of Organic Chemistry is generally based on the IUPAC nomenclature rules, even though certain deviations or extrapolations therefrom are often employed. This will be taken into account where appropriate.
D. Hellwinkel

Literature

Abstract
The standard IUPAC manual on systematic Nomenclature of Organic Chemistry1 has recently been supplemented by a “Guide” promulgating current developments in this domain2. A wealth of excellent illustrative material concerning the application of systematic nomenclature to ring compounds is presented in the Ring Index3. Important topical revisions and extensions of the nomenclature for fused rings4, von Baeyer polycycles5, spiro compounds6, and cyclophanes7 complement the older compendia. Since in the framework of the registry and index systems of Chemical Abstracts not only unambiguous but to a much greater extent unique names are required, further subtilizations and extensions of the IUPAC rules have been effectuated there. Details are given in the so-called Index Guides attached to the respective five-year indexes8. The same holds for the particular interpretations of the IUPAC rules in Beilstein’s Handbook of Organic Chemistry — regrettably these are not generally accessible. Detailed rules for the nomenclature of biochemistry and natural products have recently been reissued9. Extensive instructions for naming metal- and metalloid-organic compounds can be found in the updated rules of Inorganic Nomenclature10 as well as in a very recent compilation in Pure and Applied Chemistry11. Also very recent is a new, thoroughly revised edition of the nomenclature recommendations for carbohydrates12. All new developments and revisions in the area of chemical nomenclature worked out by the IUPAC nomenclature commissions are routinely published in the Journal of Pure and Applied Chemistry.
D. Hellwinkel

1. Parent Structures

Abstract
Saturated hydrocarbons are classified by the parent name alkanes; substituent groups derived from them are called alkyl (or alkanyl, see below) groups. The naming system is based on the unbranched members of the homologous series CnH2n+1 of which only the first four are designated by trivial names.
D. Hellwinkel

2. Substituted Systems

Abstract
The notion of a “substituent”, which has already been repeatedly used in the discussions of substituent groups derived from parent structures, will obviously occupy a central position in the following sections and therefore requires a broadened definition.
D. Hellwinkel

3. Brief Demonstration of the General Nomenclature Rules for the Most Important Traditional Compound Classes (Functional Parents)

Abstract
Because the use of different kinds of nomenclature for one and the same compound class is still widespread, it is necessary to bring into focus which principles are to be applied in general. However, only those compound classes will be discussed individually whose naming does not axiomatically follow from Table 8. As a rule, frequently occurring trivial names are compiled in tables in the appendix. The remaining compound classes are mentioned in the examples. Incidentally, it should be noted once again that in the context of substitutive nomenclature certain class names no longer appear at all in the names of the pertinent individual compounds, as in the case of alcohols, ethers, ketones, etc.
D. Hellwinkel

4. Metalorganic and Metalloidorganic Compounds

Abstract
On account of the plethora of organometall(oid)ic compounds and the ever contentious question of their assignment to organic chemistry on the one hand or inorganic chemistry on the other, the development of a binding systematic nomenclature for this domain always was and still is fraught with major difficulties and is thus far from being settled. All that can be given here, therefore, is just a survey of current practice supplemented by sketches of a future scenario determined by emerging tendencies towards tighter systematization. Meanwhile it has become abundantly clear that at least two naming variants will ultimately persist: one organic, substitutive, and one inorganic, coordinative.
D. Hellwinkel

5. Carbohydrates

Abstract
It goes without saying that by strictly applying the rules of subtitutive nomenclature, all carbohydrates and their derivatives could readily and uniformly be named as polyhydroxyalkanals, -alkanones, -tetrahydrofurans, -tetrahydropyrans, -oxepanes, -alkanoic acids, etc. which would, however, require supplementing by a more or less extended set of stereodescriptors. It is precisely this last problem which in the specific framework of carbohydrate nomenclature has been solved in a distinctly different and certainly much clearer manner, in that numerous stereochemically unambiguously defined trivial and semitrivial names have been installed as cornerstones of the body of rules. The pertinent rule manual has recently been published in a thoroughly revised edition but its fundamental systematic features, as presented in the following paragraphs, should also be familiar to the non-specialist.
D. Hellwinkel

6. Construction of the Names of Complex Compounds

Abstract
Chapters 1, Chapter 2, and Chapter 3 of this book have dealt in some detail with the nomenclature rules for parent structures and the wealth of different functional compound classes based there upon. The present chapter will recapitulate once again in a more summary manner the most important directives for the construction of the complete names of more complex compounds. This entails a reconsideration of the question of priorities for ring and chain systems already briefly approached in the pertinent sections of Chapter 1. Since functional groups must ultimately be included in the decisions, extension of the priority rules becomes imperative, as will be shown in the following sections.
D. Hellwinkel

7. Appendix

Without Abstract
D. Hellwinkel

Backmatter

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