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For nomenclature purposes, a structure containing at least one carbon atom is considered to be an organic compound and can be named using the principles of organic nomenclature, such as substitutive or replacement nomenclature, as described in this book.
- 5MB
- 91
- G.J. LEIGH OBE
- Preface
- PREFACE
- viii Introduction
- (IUPAC) and its Commission on Nomenclature of Organic Chemistry (CNOC),
- 2 2 Definitions
- For a longer list, see Table 2.1. For the heavier elements as yet unnamed or
- CHAPTER 3
- FORMULAE
- 12. [{Fe(CO)3}3(CO)2]2
- CHAPTER 3
- Where there are no overriding requirements, the following criteria may be
- RnXeKrArNeHeB SiC SbAsPNHTeSe SAtIBrC1OF
- 29. C1CHCH2CH2CH2CH2CH2
- Fischer projection (b)
- e ,a
- CHAPTER 3
- HHHHHHHH
- CHAPTER 3
- 3.8.2 Conformational isomers (or conformers)
- CHAPTER 3
- 4.1 TYPES OF NOMENCLATURE
- Initially, the names were always trivial, because the systematics of molecular
- 4.1.1 Binary-type nomenclature
- 4.2.1 Basis of the binary system
- CHAPTER 4
- Hydrogen is an exception. It is always cited last among the electropositive
- If there is more than one electronegative constituent the names are ordered
- Cl
- Cr02
- Na
- Name
- Zr
- NAMING OF SUBSTANCES
- These are based on the usage of substitutive nomenclature, where the formal
- 4.3 MORE COMPLEX NOMENCLATURE SYSTEMS
- CHAPTER 4
- NAMING OF SUBSTANCES
- OCl
- NAMING OF SUBSTANCES
- NAMING OF SUBSTANCES
- An oxoacid is a compound that contains oxygen and at least one hydrogen atom
- For a more detailed treatment, the reader is referred to the Nomenclature of
- Substitutive nomenclature was developed using the concepts that governed the
- The principal ring is selected using the criteria in Table 6.1. For instance,
- Compounds composed of rings and chains are also named using substitutive
- NAMING OF SUBSTANCES
- Names of functional parent hydrides
- Names of substituted derivatives
- • A monomeric unit is the largest constitutional unit contributed by a single
- • A regular polymer is a substance composed of regular macromolecules, the
- CHAPTER 6
- 6.2 GENERAL CONSIDERATIONS
- CHAPTER 6
- Cl
- -CH2-O-CH-
- MACROMOLECULAR NOMENCLATURE
- —E N-CH2-NH—_-)— poly[(methylimino)methyleneimino-l ,3-phenylene]
- In a double-strand polymer, the macromolecules consist of an uninterrupted se-
- 6.4.3 Regular single-strand inorganic and coordination polymers
- The constituent subunit of highest seniority must contain one or more central
- Cu— ?
- 6.4.4 Regular quasi-single-strand coordination polymers
- Irregular single-strand organic polymers
- —CH-CH2-
- —CH-, —C-, —CH-
- PP
- 7.2 CARBOHYDRATE NOMENCLATURE
- Y = CH2OH
- Glu Cys rlL -Gly
- 7.4 LIPID NOMENCLATURE
- There are saponifiable lipids, such as acylglycerols (fats and oils), waxes and
- 7.5 STEROID NOMENCLATURE
- An area of current development is the nomenclature of organometallic com-
The School of Chemistry, Physics and Environmental Science, University of Sussex, Brighton, UK
This book arose out of the convictions that IUPAC nomenclature needs to be made as accessible as possible to teachers and students alike, and that there is an absence of relatively complete accounts of the IUPAC 'colour' books suited to school and undergraduate audiences. This is not to decry in any way the efforts of organisations such as the Asso...
good reason why chemists generally should not adopt the more systematic phos- phane, rather than phosphine, for PH3. Students may find this matter of choice confusing on occasion, which will be a pity. However, there are certain long-established principles that endure, and we hope to have encompassed them in this book.
Chemical nomenclature is at least as old as the pseudoscience of alchemy, which was able to recognise a limited number of reproducible materials. These were assigned names that often conveyed something of the nature of the material (vitriol, oil of vitriol, butter of lead, aqua fortis . . .). As chemistry became a real science, and principles of th...
which has the remit to study all aspects of the nomenclature of organic substances, to recommend the most desirable practices, systematising trivial (i.e. non-systematic) methods, and to propose desirable practices to meet specific problems. The Commis- sion on the Nomenclature of Inorganic Chemistry (CNIC) was established rather later, because of ...
An element (or an elementary substance) is matter, the atoms of which are alike in having the same positive charge on the nucleus (or atomic number). In certain languages, a clear distinction is made between the terms 'element' and 'elementary substance'. In English, it is not customary to make such nice distinc-tions, and the word 'atom' is someti...
unsynthesised, the three-letter symbols, such as Uuq, and their associated names are provisional. They are provided for temporary use until such time as a consensus is reached in the chemical community that these elements have indeed been synthe- sised, and a trivial name and symbol have been assigned after the prescribed IUPAC procedures have take...
Polyatomic ions are treated similarly, although the charge must also be indicated. These formulae tell nothing about structure. As soon as structural information is combined with the formula, these simple rules need to be amplified. It should be noted that the discussion so far has assumed that all compounds are stoichiometric, i.e. that all the at...
In organic chemistry, structural formulae are frequently presented as condensed formulae. This abbreviated presentation is especially useful for large molecules. Another way of presenting structural formulae is by using bonds only, with the understanding that carbon and hydrogen atoms are never explicitly shown. Examples
Note the use of enclosing marks: parentheses Q,square brackets [] and braces { }. They are used to avoid ambiguity. In the specific case of coordination compounds, square brackets denote a 'coordination entity' (see below). In the organic examples above, the use of square brackets to indicate an unbranched chain is shown. In organic nomenclature ge...
modified alphabetical sequence is recommended. This is primarily a sequence for use in indexes, such as in a book that lists compounds cited by formula.
adopted for general use. In a formula, the order of citation of symbols is based upon relative electronegativities. Although there is no general confusion about which of, say, Na and Cl represents the more electronegative element, there is no universal scale of electronegativity that is appropriate for all purposes. However, for ionic compounds, ca...
For intermetallic compounds, where all the elements can be considered to be electropositive, strict alphabetical ordering of symbols is recommended. Examples
Note that these bond indicators do not imply long bonds. Their size and form are dictated solely by the demands of the linear presentation. It is usual for a coordination compound to write the formula of a ligand with the donor atom first. The nickel complex represented above has both S and P bonded to the metal (as well as all the carbon atoms of ...
Note that some authorities prefer to use a thickened line to represent a bond projecting towards the reader, and that organic practice is never to indicate a carbon atom in a projection by an atomic symbol. A Newman projection is obtained by viewing a molecule along a bond. Take the ethane (or substituted ethane) molecule represented below (a). Thi...
dC—C,-b f c Three-dimensional structure (a) I b e f
The Newman projection along the central carbon—carbon bond is shown below. d a f b Newman projection A circle represents these two carbon atoms, with lines from outside the circle towards its centre representing bonds to other atoms. The lines that represent bonds to the nearer carbon atom end meet at the centre, and those to the other carbon atom ...
synperiplanar (sp) synclinal (sc) anticlinal (as) antiperiplanar (ap) or gauche Note that the terms syn and anti alone are no longer used in this context. The chlorine atoms may be described as synperiplanar, synclinal, anticlinal or anti- periplanar to each other. In inorganic compounds, stereochemical arrangements other than octahedral or tetrahe...
different alkanes differing from each other in their connectivities. Two are shown in
The conformation of a molecule is the spatial arrangement of the atoms. Different stereoisomers that can be interconverted by rotation about single bonds are termed conformers. Thus a conformer is one of a set of stereoisomers differing from one another in their conformations, each of which is considered to correspond to a potential-energy minimum....
mirror images of each other. Where two such molecules exist in chemistry, they are called enantiomers. Enantiomers have identical physical properties (except for the interaction with polarised light) and chemical reactivity (except for reaction with other chiral species). Consequently, any biological activities that involve stereospec-ificity may a...
Specialists in nomenclature recognise two different categories of nomenclature. Names that are arbitrary (including the names of the elements, such as sodium and hydrogen) as well as laboratory shorthand names (such as diphos and LithAl) are termed trivial names. This is not a pejorative or dismissive term. Trivial nomencla-ture contrasts with syst...
structure were completely unknown. The names of the elements are still essentially trivial, but these are the basis of systematic nomenclature. Now that we understand much more of the way in which atoms combine, we can construct names that can give information about stoichiometry and structure. However, unsystematic usages that have their roots in ...
This is a system based upon stoichiometry. It is not restricted to binary (two-element) compounds, but the nomenclature is binary in structure, as discussed below.
This provides names for compounds for which little or no structural information is available. However, a minimum of structural information is known or assumed. In particular, using the assumed or established division of constituents into positive and negative parts already employed above in establishing formulae, we divide the constituents into the...
multiplicative prefixes. The electropositive constituent names are cited first, and are separated from the electronegative constituent names by a space. The multiplicative prefixes may not be necessary if the oxidation states are explicit or are clearly understood. However, oxidation state information should never be conveyed by the suffixes -ous a...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
pounds. Organometallic compounds of Main Group elements can, to a first approx-imation, be considered to be derivatives of hydrides, and the methods of substitutive nomenclature can be applied. Even then, the accessibility of different oxidation states, as with phosphorus(ni) and phosphorus(v), introduces complications. Transi- tion metal organomet...
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precise and accurate nomenclature is a vital aspect of professional training in the discipline of chemistry, few teachers, and fewer students, felt the need to master it. It has often been possible to convey information by using customary short and familiar names. However, that is as if the familiar and
illustrated with reference to the chemical structure shown in Table 1, along with its systematic name and the components of the name. Locants indicate the position of substituents or other structural
Nomenclature addresses the connection between common names, systematic names and chemical formulas.Common names require some form of table lookup.Systematic names are derivedfrom classifying the substance and applying the appropriate nomenclature rules. Conventional nomenclature rules can be found in specific publications devoted to nomencla-
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IUPAC Division of Chemical Nomenclature and Structure Representation. The universal adoption of an agreed nomenclature is a key tool for efficient communication in the chemical sciences, in industry and for regulations associated with import/export or health and safety.
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This edition of the Nomenclature of Organic Chemistry follows the 1993 publication of the Guide to IUPAC Nomenclature of Organic Compounds by the International Union of Pure and Applied Chemistry (IUPAC).
