Chemical Nomenclature and Structure
Representation Division
Nomenclature of Organic Chemistry
For nomenclature purposes, a structure containing at
least one carbon atom is considered to be an organic compound. The
formation of a systematic name for an organic compound requires selection
and then naming of a parent structure. This basic name may then be
modified by prefixes, infixes, and, in the case of a parent hydride,
suffixes, which convey precisely the structural changes required to
generate the compound in question from the parent structure. In contrast
to such systematic names, there are traditional names which are widely
used in industry and academic circles. Examples are acetic acid, benzene
and pyridine. Therefore, when they meet the requirements of utility
and when they fit into the general pattern of systematic nomenclature,
these traditional names are retained.
A major new principle is elaborated in these Recommendations.
The concept of preferred IUPAC names is developed and
systematically applied. Up to now, the nomenclature developed and
recommended by IUPAC has emphasized the generation of unambiguous
names in accord with the historical development of the subject. In
1993, due to the explosion in the circulation of information and the
globalization of human activities, it was deemed necessary to have
a common language that will prove important in legal situations, with
manifestations in patents, export-import regulations, environmental
and health and safety information, etc. However, rather than recommend
only a single unique name for each structure, we have
developed rules for assigning preferred IUPAC names, while
continuing to allow alternatives in order to preserve the diversity
and adaptability of the nomenclature to daily activities in chemistry
and in science in general.
Thus, the existence of preferred IUPAC names does not
prevent the use of other names to take into account a specific context
or to emphasize structural features common to a series of compounds.
Preferred IUPAC names belong to preferred IUPAC nomenclature
Any name other than a preferred IUPAC name, as long as it is unambiguous
and follows the principles of the IUPAC recommendations herein, is
acceptable as a general IUPAC name, in the context of
general IUPAC nomenclature. The concept of preferred IUPAC
names is developed as a contribution to the continuing evolution of
the IUPAC nomenclature of organic compounds. This book (Recommendations
2004) covers and extends the principles, rules and conventions described
in two former publications: Nomenclature of Organic Chemistry, 1979
Edition and A Guide to IUPAC Nomenclature of Organic Compounds, Recommendations
1993. In a few instances, the 1979 rules and the 1993 recommendations
have been modified to achieve consistency within the entire system.
In case of divergence among the various recommendations, Recommendations
2004 prevail.
> Download full text of the Provisional Recommendations from the
CONTENTS below. Alternatively, and to facilitate full
text searching, the whole volume as single pdf is also available [pdf
- 10.34MB].
In addition, a file compiling the changes made in this new edition
and compare to the 1979 edition and the 1993 Guide is also available
[pdf - 96KB].
Comments by 31 March 2005
To Prof. Henri A. Favre
2031 Rue Leclaire
Montréal, QC H1V 3A1
Canada
TEL: +1 514 259 7963
E-MAIL: [email protected]
|
|
and to Dr. Warren H. Powell
1436 Havencrest Court
Columbus, OH 43220-3841
USA
TEL: +1 614 451 1830
E-MAIL: [email protected]
|
CONTENTS
CHAPTER P-1 NOMENCLATURE OF ORGANIC COMPOUNDS [pdf
- 936KB]
P-10 Introduction
P-11 Scope of nomenclature of organic compounds
P-12 Preferred, preselected and retained names
P-13 Operations in nomenclature
P-14 General rules
P-15 Types of nomenclature
P-16 Name writing
CHAPTER P-2 PARENT HYDRIDES
P-20 Introduction [P-20 to P-24, pdf
- 558KB]
P-21 Mononuclear and polynuclear acyclic parent hydrides
P-22 Monocyclic hydrides
P-23 Polyalicyclic (von Baeyer) systems
P-24 Spiro compounds
P-25 Fused and bridged fused systems [pdf
- 727KB]
P-26 Phane nomenclature [P-26 to P-29, pdf
- 636KB]
P-27 Fullerenes
P-28 Ring assemblies
P-29 Prefixes denoting substituent groups derived from parent hydrides
CHAPTER P-3 CHARACTERISTIC (FUNCTIONAL) GROUPS [pdf
- 441KB]
P-30 Introduction
P-31 Modification of the degree of hydrogenation of parent hydrides
P-32 Prefixes for substituent groups derived from parent hydrides with
a modified degree of hydrogenation
P-33 Suffixes
P-34 Parent structures other than parent hydrides and corresponding
prefixes for substituent groups
P-35 Prefixes denoting characteristic groups
CHAPTER P-4 RULES FOR NAME CONSTRUCTION [pdf
- 710KB]
P-40 Introduction
P-41 Seniority order of classes
P-42 Seniority order of acids
P-43 Seniority order of suffixes
P-44 Seniority order of parent structures
P-45 The principal chain in substituent groups
P-46 Substitution rules for parent structures with retained names
CHAPTER P-5 CONSTRUCTING PREFERRED IUPAC NAMES [pdf
- 523KB]
P-50 Introduction
P-51 Selecting the preferred type of nomenclature
P-52 Selecting preferred IUPAC names and preselected names (see P-12)
for parent hydrides names
P-53 Selecting the preferred method for modifying the degree of hydrogenation
for parent hydrides
P-54 Selecting the preferred suffix (principal group)
P-55 Selecting preferred retained names
P-56 Selecting preferred substituent group names
P-57 Selecting preferred names for tautomeric compounds
P-58 Name construction
CHAPTER P-6 APPLICATIONS TO SPECIFIC CLASSES OF COMPOUNDS
P-60 Introduction [P-60 to P-64, pdf
- 666KB]
P-61 Substitutive nomenclature: prefix mode
P-62 Amines and imines
P-63 Hydroxy compounds, ethers, peroxols, peroxides and chalcogen analogues
P-64 Ketones, pseudo ketones and heterones, and chalcogen analogues
P-65 Acids and derivatives [pdf
- 613KB]
P-66 Amides, hydrazides, nitriles, aldehydes [pdf
- 561KB]
P-67 Oxoacids used as parents for organic compounds [pdf
- 365KB]
P-68 Nomenclature of other classes of compounds [pdf
- 524KB]
P-69 Organometallic compounds [pdf
- 153KB]
CHAPTER P-7 RADICALS, IONS, AND RELATED SPECIES [pdf
- 655KB]
P-70 General methodology
P-71 Radicals
P-72 Anions
P-73 Cations
P-74 Zwitterions
P-75 Radicals ions
P-76 Delocalized radicals and ions
P-77 Preferred names
CHAPTER P-8 ISOTOPICALLY MODIFIED COMPOUNDS [pdf
- 194KB]
P-80 Introduction
P-81 Symbols and definitions
P-82 Isotopically substituted compounds
P-83 Isotopically labelled compounds
P-84 Comparative examples of formulae and names of isotopically modified
compounds
CHAPTER P-9 SPECIFICATION OF CONFIGURATION AND CONFORMATION
[pdf - 905KB]
P-90 Introduction
P-91 CIP Priority and sequence rules
P-92 Configurational stereodescriptors
P-93 Applications of stereodescriptors
P-94 Conformation and conformational stereodescriptors
CHAPTER P-10 PARENT STRUCTURES FOR NATURAL PRODUCTS AND RELATED
COMPOUNDS [pdf - 1.05MB]
P-100 Introduction
P-101 Nomenclature for natural products based on parent hydrides (alkaloids,
steroids, terpenes, carotenes, corrinoids, tetrapyrroles, and similar
compounds)
P-102 Carbohydrate nomenclature
P-103 Amino acids and peptides
P-104 Cyclitols
P-105 Nucleosides
P-106 Nucleotides
P-107 Lipids
REFERENCES [pdf - 37KB]
APPENDIX 1 [pdf - 18KB]
Seniority list of elements and 'a' terms used in replacement ('a') nomenclature
in decreasing order of seniority
APPENDIX 2 [pdf - 308KB]
Usual detachable prefixes used in substitutive nomenclature
> 'Preferred
names' Project Description