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IUPAC numerical multiplier

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IUPAC numerical multiplier

The numerical multiplier (or multiplying affix) in IUPAC nomenclature indicates how many particular atoms or functional groups are attached at a particular point in a molecule. The affixes are derived from both Latin and Greek.

The prefixes are given from the least significant decimal digit up: units, then tens, then hundreds, then thousands. For example:

While the use of the affix mono- is rarely necessary in organic chemistry, it is often essential in inorganic chemistry to avoid ambiguity: carbon oxide could refer to either carbon monoxide or carbon dioxide. In forming compound affixes, the numeral one is represented by the term hen- except when it forms part of the number eleven (undeca-): hence

In compound affixes, the numeral two is represented by do- except when it forms part of the numbers 20 (icosa-), 200 (dicta-) or 2000 (dilia-).

IUPAC prefers the spelling icosa- for the affix corresponding to the number twenty on the grounds of etymology. However both the Chemical Abstracts Service and the Beilstein database use the alternative spelling eicosa-.

There are two more types of numerical prefixes in IUPAC organic chemistry nomenclature.

Numerical prefixes for multiplication of compound or complex (as in complicated) features are created by adding kis to the basic numerical prefix, with the exception of numbers 2 and 3, which are bis- and tris-, respectively.

An example is the IUPAC name for DDT (1,1,1-Trichloro-bis-2,2(4-chlorophenyl)ethane).

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