IUPAC rules of nomenclature for

As we cover new functional groups in later chapters, the applicable IUPAC rules of nomenclature will be given. In addition, Appendix A at the back of this book gives an overall view of organic nomenclature and shows how compounds that contain more than one functional group are named. For the present, let s see how to name branched-chain alkanes and learn some general naming rules that are applicable to all compounds. 

The nomenclature for this homologous series is somewhat confused. The term PANs has been used historically to denote peroxyacyl nitrates, and this terminology continues to be used extensively in the literature, despite the lack of adherence to traditional IUPAC rules of nomenclature. Because the PANs can be considered to be mixed anhydrides of carboxylic acids and nitric acid, another suggestion (Roberts, 1990) has been peroxyacetic nitric anhydride for CH,C(0)00NO2 and peroxy carboxylic nitric anhydrides for the whole class of compounds. Although it does not follow the IUPAC rules, it would be consistent with the widespread use of the name PAN but also reflect the structure more accurately. Table 6.20 shows the structures and commonly used names of some PANs that have been observed in the atmosphere and/or in laboratory studies. 

One particular domain in which the alternate method of naming is of significance is that of natural products (perhaps, because of the occurrence of many ring assemblages). Note that this is a domain which, because of the complexity of the IUPAC nomenclature, has opted to formulate its own set of parochial rules of nomenclature, in much the same way as the organic chemistry community formulated IUPAC nomenclature to include 35 "basis" aromatic compounds on which all other "comparable" compounds were to be named [18], This is in contradistinction to various systematic approach, such as a geometry-based proposals for the fusion of benzene modules [19] and for general arenes [20],... 

As noted in the text, chemists overwhelmingly use the nomenclature system devised and maintained by the International Union of Pure and Applied Chemistry, or IUPAC. Rules for naming monofunctional compounds were given throughout the text as each new functional group was introduced, and a list of where these rules can be found is given in Table A.l. 

In this book we use the Nomenclature of Organic Chemistry of the International Union of Pure and Applied Chemistry, 1979 Edition ( Blue book , IUPAC, 1979), the Revised Nomenclature for Radicals, Ions, Radical Ions, and Related Species (IUPAC, 1993), and additional rules applied by the Chemical Abstracts Service for the 1987-1991 Index Guide Chemical Abstracts, 1992). 

In aromatic diazonium compounds containing an ionized hydroxyl group ( —O-) in the 2- or 4-position, it is necessary to consider delocalization of electrons and, therefore, two mesomeric structures (1.7a-1.7b) (see Sec. 4.2). This fact has implications for nomenclature compounds of this type are considered as quinone derivatives following IUPAC Rule C-815.3 (Exception) compounds of this class are called quinone diazides. As a specific compound 1.7a-1.7b is indexed in Chemical Abstracts as 4-diazo-2,5-cyclohexadien-l-one. If reference is made specifically to mesomeric structure 1.7b, however, it is called 4-diazoniophenolate. 

Not all problems were solved, however, and different usages were encountered on the two sides of the Atlantic. A joint British-American committee was therefore set up, and in 1952 it published Rules for Carbohydrate Nomenclature [18]. This work was continued, and a revised version was endorsed in 1963 by the American Chemical Society and by the Chemical Society in Britain and published [19]. The publication of this report led the IUPAC Commission on Nomenclature of Organic Chemistry to consider the preparation of a set of IUPAC Rules for Carbohydrate Nomenclature. This was done jointly with the IUPAC-IUB Commission on Biochemical Nomenclature, and resulted in the Tentative Rules for Carbohydrate Nomenclature, Part I, 1969 , published in 1971/72 in several journals [1]. It is a revision of this 1971 document that is presented here. In the present document, recommendations are designated 2-Carb-n, to distinguish them from the Carb-n recommendations in the previous publication. 

The nomenclature of boron compounds involves some intricacies. IUPAC rules allow the terms borabenzene or borinine for 2 the older name borin has become obsolete with the recent revision of the extended Hantzsch-Widman system (6). Anions 4 are termed boratabenzene ions an alternative would be borininate instead of the earlier borinate (7). 

It is of course possible to name individual radialenes according to IUPAC rules [e.g. per(methylene)cycloalkanes 1-4]. However, the descriptiveness of the term radialene may some day pave its way into the official nomenclature. For substituted [ ]radialenes we have proposed1 a pragmatic numbering system, in which an inner ring is numbered first, followed by an outer ring . The numbering of substituents should follow IUPAC rules. Thus, the hydrocarbon 7 is 4,4-diethyl-5,5-dimethyl[3]radialene, the ester 8 should be called 7-methoxycarbonyl-5,5-dimethyl[4]radialene, the nitrile 9 which can exist in four diastereomeric forms is (6Z,7Z)-6-cyano-5,5,7-trimethyl[4]radialene and the difunctionalized [5]radialene 10 is (7 ,6Z)-7-bromo-6-formyl-6-methyl[5]radialene. 

Since atropisomers are conformational isomers, their stereochemistry should be designated by IUPAC nomenclature rule E (23). For the convenience of the reader, the rule will be outlined here. A sequence number is given to substituents connected to the rotational axis according to the Sequence Rule (24), as follows. 

The IUPAC nomenclature will be used in this book with some exceptions. One exception is the use of well-established, non-IUPAC names for most of the commonly encountered polymers of commercial importance. Another exception will be in not following rule 2 for writing the constitutional repeating unit (although the correct IUPAC name will be employed). Using the IUPAC choice of the CRU leads in some cases to structures that are longer and appear more complicated. Thus the IUPAC structure for the polymer in Eq. 1-3 is... 

Before proceeding one needs to mention Chemical Abstracts (CA), a journal published by the American Chemical Society, that abstracts the world s chemical hterature and has developed its own nomenclature rules. The CA rules are generally very close to the IUPAC rules, but there are some differences. Most of the differences are not important at the level of the discussions in this book. One difference that needs to be mentioned is the placement of locants. CA does not place locants immediately before the part of the name to which they apply. Thus, the CA name for the first subunit in XV is 2,4-pyridinediyl instead of pyridine-... 

The fusion name l/7-triazolo[4,5-rf]pyrimidine for (140) is preferred by practitioners in the field and appears in CA indexes. On the other hand, the nonspecialist, who may well be uncertain about his command of fusion nomenclature, might more easily grasp the replacement name l//-l,2,3,4,6-pentaazaindene. (This is an appropriate place to emphasize that, by IUPAC rules, replacement names are to be based only on a completely carbocyclic parent. Notwithstanding the attractive simplicity of 8-azapurine for the example at hand, it has no sanction see, however, Section 1.02.3.2. The purpose of this avoidance is to forestall a multiplicity of names for systems containing several hetero atoms.)... 

This chapter presents a concise overview of the present conventions in coordination nomenclature. Generally, the IUPAC rules and recommendations have been followed. For the cases where the IUPAC practices seemed to be out of date or incomplete, the author has drawn upon the vast expertise in nomenclature available at Chemical Abstracts Service. Sections 3.2.3 and 3.4 deal with ligand locant notation and the numbering of polynuclear complexes may be considered provisional. These concepts are still under active consideration in the various national and international nomenclature commissions and committees. The presentation is relatively brief, but it is hoped that the nomenclature principles are evident, especially when examples presented are closely... 

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