R-0.1.4 Numerical (multiplicative) prefixes

These are derived from Greek and Latin number names and are the principal method for describing a multiplicity of identical features of a structure in chemical nomenclature (see R-4.1, especially Table 11).

R- The simple numerical prefixes "di-", "tri"-, "tetra-", etc., are of Greek derivation (except for "nona-" and "undeca-", which are derived from Latin) and are used to indicate a multiplicity of substituent suffixes, conjunctive components, replacement affixes, simple (i.e., unsubstituted) substituent prefixes, and simple (i.e., unsubstituted) functional modification terms provided that there is no ambiguity (see also R-

Examples to R-

-diol ditetradecane-1,14-diyl-
-dicarboxylic acid tetra-2-naphthyl-
tricyclohexyl- dioxime
ditridecyl- dibenzenesulfonate
-diamido- ethylenediimino-
diaza- diisoxazol-3-yl-
Benzene-1,3,5-triacetic acid (R-

R- The numerical prefixes "bis-", "tris-", "tetrakis-", etc., which, except for "bis-" and "tris-", are derived by adding "kis-" to the simple numerical prefixes (see Table 11), are used to indicate a multiplicity of substituted substituent prefixes or functional modification terms.

Examples to R-




Such prefixes are also used when the use of "di-", "tri-", etc., is (or could be) ambiguous; this usually happens when an analogue of the term being multiplied being with a simple numerical prefix.

Examples to R-



bis(ylium) (R-5.8.2)




R- The numerical prefixes "bi-", "ter-", "quater-", etc., are derived Latin number names and are used mainly in ring assembly names.

Examples to R-

Biphenyl (R-2.4.4)

2,2':6',2":6",2'"-Quaterpyridine (R-2.4.4)

R- The prefix "mono-" is usually omitted in chemical names. However, it is used to indicate that only one characteristic group of a parent structure has been modified. The ending "-kis" is not used with "mono-".

Examples to R-

Monoperoxyterephthalic acid (R-

Phthalic acid monomethyl ester (R-

R-0.1.5 Enclosing marks
R-0.1.6 Italicization
R-0.1.7 Elision and addition of vowels
R-0.1.8 Order of prefixes

This HTML reproduction is as close as possible to the published version [see IUPAC, Commission on Nomenclature of Organic Chemistry. A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993), 1993, Blackwell Scientific publications, Copyright 1993 IUPAC]. If you need to cite these rules please quote this reference as their source.

Published with permission of the IUPAC by Advanced Chemistry Development, Inc.,, +1(416)368-3435 tel, +1(416)368-5596 fax. For comments or suggestions please contact