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Introduction

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-0.1.4.1 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-0.1.4.2).

Examples to R-0.1.4.1

-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-1.2.4.1)

R-0.1.4.2 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-0.1.4.2

bis(2-aminoethyl)-

ethylenebis(oxymethylene)-

bis(phenylhydrazone)

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-0.1.4.2

tris(methylene)-

tris(decyl)-

bis(ylium) (R-5.8.2)

bis(phosphate)

bis(benzo[a]anthracen-1-yl)-

Benzo[1,2-c:3,4-c']bis[1,2,5]oxadiazole

R-0.1.4.3 The numerical prefixes "bi-", "ter-", "quater-", etc., are derived Latin number names and are used mainly in ring assembly names.

Examples to R-0.1.4.3

Biphenyl (R-2.4.4)

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

R-0.1.4.4 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-0.1.4.4

Monoperoxyterephthalic acid (R-5.7.1.3.1)

Phthalic acid monomethyl ester (R-5.7.4.2)

Next:
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
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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.

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