Substitutive prefixes

Formula Parent name Substitutive prefix ending... 

The exchange of one or more hydrogen atoms for another atom or group can be denoted by a substitutive prefix or suffix (example 143). 

Table 7 Common Substituent Groups and the Corresponding Substitutive Prefixes and/or Suffixes...

Isocyanides and analogous compounds are exclusively named in a radico-functional way, i.e. with functional class designations, provided the functional group is not expressed as a substitutive prefix. 

In contrast, all substitutive prefixes (Tables 6,8) are treated as detachable and ordered alphabetically. 

Substitutive lUPAC nomenclature names epoxides as epoxy derivatives of alkanes According to this system ethylene oxide becomes epoxyethane and propylene oxide becomes 1 2 epoxypropane The prefix epoxy always immediately precedes the alkane ending it is not listed m alphabetical order like other substituents... 

All compounds that contain a benzene ring are aromatic and substituted derivatives of benzene make up the largest class of aromatic compounds Many such compounds are named by attaching the name of the substituent as a prefix to benzene... 

Organometallic compounds are named as substituted derivatives of metals The metal is the parent and the attached alkyl groups are identified by the appropriate prefix... 

Ethers are named m substitutive lUPAC nomenclature as alkoxy derivatives of alkanes Functional class lUPAC names of ethers are derived by listing the two alkyl groups m the general structure ROR m alphabetical order as separate words and then adding the word ether at the end When both alkyl groups are the same the prefix di precedes the name of the alkyl group... 

Secondary and tertiary amines are named as N substituted derivatives of primary amines The parent primary amine is taken to be the one with the longest carbon chain The prefix N is added as a locant to identify substituents on the ammo nitrogen as needed... 

Table 1.8 Characteristic Groups Cited Only as Prefixes in Substitutive...

Substitution means the replacement of one or more hydrogen atoms in a given compound by some other kind of atom or group of atoms, functional or nonfunctional. In substitutive nomenclature, each substituent is cited as either a prefix or a suffix to the name of the parent (or substituting radical) to which it is attached the latter is denoted the parent compound (or parent group if a radical). 

In Table 1.8 are listed characteristic groups that are cited only as prefixes (never as suffixes) in substitutive nomenclature. The order of listing has no significance for nomenclature purposes. 

Systematic names formed by applying the principles of substitutive nomenclature are single words except for compounds named as acids. First one selects the parent compound, and thus the suffix, from the characteristic group listed earliest in Table 1.7. All remaining functional groups are handled as prefixes that precede, in alphabetical order, the parent name. Two examples may be helpful ... 

If the characteristic group occurs only in a chain that carries a cyclic substituent, the compound is named as an aliphatic compound into which the cyclic component is substituted a radical prefix is used to denote the cyclic component. This chain need not be the longest chain. 

When a substituent is itself substituted, all the subsidiary substituents are named as prefixes and the entire assembly is regarded as a parent radical. 

Acid Anhydrides. Symmetrical anhydrides of monocarboxylic acids, when unsubstituted, are named by replacing the word acid by anhydride. Anhydrides of substituted monocarboxylic acids, if symmetrically substituted, are named by prefixing bis- to the name of the acid and replacing the word acid by anhydride. Mixed anhydrides are named by giving in alphabetical order the first part of the names of the two acids followed by the word anhydride, e.g., acetic propionic anhydride or acetic propanoic anhydride. Cyclic anhydrides of polycarboxylic acids, although possessing a... 

A-substituted primary amides are named either (1) by citing the substituents as N prefixes or (2) by naming the acyl group as an N substituent of the parent compound. For example. 

Ethers (R —O—R ). In substitutive nomenclature, one of the possible radicals, R—O—, is stated as the prefix to the parent compound that is senior from among R or R. Examples are methoxyethane for CH3OCH2CH3 and butoxyethanol for C4Hc,0CH2CH20H. 

Halogen Derivatives. Using substitutive nomenclature, names are formed by adding prefixes listed in Table 1.8 to the name of the parent compound. The prefix perhalo- implies the replacement of all hydrogen atoms by the particular halogen atoms. 

Compounds of the type R NH—OR are named (1) as alkoxyamino derivatives of compound R H, (2) as A, 0-substituted hydroxylamines, (3) as alkoxyamines (even if R is hydrogen), or (4) by the prefix aminooxy- when another substituent has priority for parent name. Examples of each type are... 

For oximes, the word oxime is placed after the name of the aldehyde or ketone. If the carbonyl group is not the principal group, use the prefix hydroxyimino-. Compounds with the group Z = N—OR are named by a prefix alkyloxyimino- as oxime O-ethers or as O-substituted oximes. Compounds with the group r C=N(0)R are named by adding A-oxide after the name of the alkylideneaminc compound. For amine oxides, add the word oxide after the name of the base, with locants. For example, C5H5N—O is named pyridine A-oxide or pyridine 1-oxide. 

Imines. The group >C=NH is named either by the suffix -imine or by citing the name of the bivalent radical R R C< as a prefix to amine. For example, CH3CH2CH2CH=NH could be named 1-butanimine or butylideneamine. When the nitrogen is substituted, as in CH2=N—CH2CH3, the name is A-(methylidene)ethylamine. 

When another group having higher priority for citation as principal group is also present, the ketonic oxygen may be expressed by the prefix 0x0-, or one can use the name of the carbonyl-containing radical, as, for example, acyl radicals and oxo-substituted radicals. Examples are... 

In order of decreasing priority for citation of a functional class name, and the prefix for substitutive nomenclature, are the following related compounds ... 

Bivalent Sulfur. The prefix thio, placed before an affix that denotes the oxygen-containing group or an oxygen atom, implies the replacement of that oxygen by sulfur. Thus the suffix -thiol denotes — SH, -thione denotes —(C)=S and implies the presence of an =S at a nonterminal carbon atom, -thioic acid denotes [(C)=S]OH [(C)=0]SH (that is, the O-substituted acid and the 5-substi-... 

The prefix thioxo- is used for naming =S in a thioketone. Sulfur analogs of acetals are named as alkylthio- or arylthio-. For example, CH3CH(SCH3)OCH3 is l-methoxy-l-(methylthio)ethane. Prefix forms for -carbothioic acids are hydroxy(thiocarbonyl)- when referring to the O-substituted acid and mercapto(carbonyl)- for the S-substituted acid. 

Organosulfur Halides. When sulfur is directly linked only to an organic radical and to a halogen atom, the radical name is attached to the word sulfur and the name(s) and number of the halide(s) are stated as a separate word. Alternatively, the name can be formed from R—SOH, a sulfenic acid whose radical prefix is sulfenyl-. For example, CH3CH2—S — Br would be named either ethylsulfur monobromide or ethanesulfenyl bromide. When another principal group is present, a composite prefix is formed from the number and substitutive name(s) of the halogen atoms in front of the syllable thio. For example, BrS—COOH is (bromothio)formic acid. 

In the case of complex entities such as organic ligands (particularly if they are substituted) the multiplying prefixes bis-, tris-, tetrakis-, pentakis-,. . . are used, i.e.,-kis is added starting from tetra-. The modified entity is often placed within parentheses to avoid ambiguity. 

Peroxo- Group. When used in conjunction with the trivial names of acids, the prefix peroxo- indicates substitution of —O— by —O—O—. 

Quaternary ammonium compounds are usually named as the substituted ammonium salt. The anion is Hsted last (3). Substituent names can be either common (stearyl) or lUPAC (octadecyl). If the long chain in the compound is from a natural mixture, the chain is named after that mixture, eg, taHowalkyL Prefixes such as di- and tri- are used if an alkyl group is repeated. Complex compounds usually have the substituents Hsted in alphabetical order. Some common quaternary ammonium compounds and their appHcations in patent Hterature are Hsted in Table 1. 

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