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Irregularity and suppletion
Now that we’ve established that all chemical names consist of content words and each content word includes at least one base, we can rephrase our original statement ix New chemical names are formed by...
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Chains and rings
After hours spent looking in my books and searching the internet, I came to the conclusion that chemists talk about chains and rings without explaining what they mean. The only definition I found so...
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Carbon chains
Introduction aside, almost every organic chemistry textbook begins with alkanes, that is, acyclic hydrocarbons with the general formula CnH2n+2. Maybe because of that, chemists tend to think of their...
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von Hofmann’s footnote
Systematic name formation in chemistry typically happens through compounding, derivation, or mix of both. The semantic modification of a combining form through umlaut-like vowel change as seen in...
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Branched hydrocarbons
How can we name the structure (a)? (a) [Sn(CH3)3H] hydridotrimethyltin (additive) trimethylstannane (substitutive) We can give it an additive name‘hydridotrimethyltin’. Alternatively, based on the...
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Alicyclic monocycles
Now let us have a look at monocyclic hydrocarbons, starting with cycloalkanes. By the way, I think this term is a bit misleading: cycloalkanes indeed contain cycles but are notalkanes because these...
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Mancude rings and annulenes
What do the structures (a), (b) and (c) have in common? (a)(b)(c) [18]annulene cyclooctadeca-1,3,5,7,9,11,13,15,17-nonaene (PIN) 1,3,5,2,4,6-triazatriphosphinine thiophene Well, it is obvious that...
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Hantzsch-Widman names
Are you tired of carbocycles? Let’s have some ring diversity, I say. Structures that contain two or more different elements in a ring are called heterocyclic. Perhaps because “heteroatom” is really an...
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The many names of crowns
What is the best way to name the structure (a)? (a) 1,4,7-trioxonane (Hantzsch-Widman) 1,4,7-trioxacyclononane (replacement) cyclo[tri(oxyethylene)] (organic macrocycle) 9-crown-3 (Pedersen)...
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Bicycles
How many rings has the structure (a)? (a) diphenyl ether (functional class) 1,1′-oxydibenzene (multiplicative) phenoxybenzene (substitutive) Why, there are two, you’ll say. Anybody can see that. And...
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von Baeyer names
Here’s a cute little structure: (a) housane (trivial) bicyclo[2.1.0]pentane (von Baeyer) Drawn like this, (a) looks like a little house and, indeed, is known as a housane. Alexander Senning called...
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Fused ring names
(a) furan (trivial, retained) oxole (Hantzsch-Widman) Knowing that the structure (a) is called furan, let’s name the structure (b).(b) 2-nitrofuran (substitutive) Easy: 2-nitrofuran. Keeping that in...
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Spiro names
Observe the structure (a). Doesn’t it look like our old friend housane after a tornado? It kept its roof but only just. (a) spiro[2.3]hexane spirohexane Let us number it in the following fashion: (a)...
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Ring assemblies
How shall we call the structure (a)?(a) biphenyl (trivial) 1,1′-biphenyl (ring assembly, PIN) phenylbenzene (substitutive) We can name it substitutively, i.e. substituting one hydrogen atom in the...
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Phane names
Have a look at the structure (a). (a) calix[4]arene (trivial) pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene (von Baeyer)...
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Inorganic chains and rings
Let’s name a simple inorganic chain (a): (a) 1,2-dinitrosodioxidane (substitutive) bis(nitrosyloxygen)(O—O) (additive) 2,5-diazy-1,3,4,6-tetraoxy-[6]catena (ICR) The shortest systematic name I can...
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λ-convention
The whole edifice of substitutive nomenclature is based on concept of parent structures, most importantly parent hydrides. Implicit in parent hydrides are the valencies, or bonding numbers, of...
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Boron hydride nomenclature
Can we expand the parent hydride naming philosophy much beyond organic chemistry? Not going too far, let’s have a peek at carbon’s immediate neighbour in the periodic table, boron. (a) BH3 borane...
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Polyhedral symbols and configuration indices
Although structural descriptors such as we’ve seen in the names of boron hydrides, for example catena or closo, provide information on atomic connectivity, they tell us little or nothing about the...
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Enantiomers
Have a look at the structures (a) and (b). (a)(b) (+)-amphetamine (trivial) d-amphetamine (trivial) dextroamphetamine (trivial) dexamfetamine (INN) (2S)-1-phenylpropan-2-amine (substitutive)...
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cis and trans
What’s the difference between the structures (a) and (b)? (a)(b) (2Z)-but-2-ene (PIN) cis-but-2-ene (2E)-but-2-ene (PIN) trans-but-2-ene Why, isn’t it obvious: in the former structure, the two methyl...
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Axial chirality
Have a look at the structures (a) and (b). They are the stereoisomers of laballenic acid, with (a) is naturally occurring in plants of the Lamiaceae family. What kind of stereoisomers are they? (a)(b)...
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Planar chirality
In most organic chemistry textbooks, double bond cis/trans isomerism is exemplified by alkenes. It is also observed in cycloalkenes such as cyclooctene that can exist as either cis(a) or trans(b)...
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α, β, ξ
Here’s a molecule everybody must have heard about: testosterone(a). (a) testosterone (INN) 17β-hydroxyandrost-4-en-3-one (fundamental parent + substitutive)...
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α and β again
The descriptors ‘α’ and ‘β’ are also used in carbohydrate nomenclature to specify configuration of cyclic monosaccharides [1, P-102.3.4.2.1]. You may remember that aldehydo-glucose, the open-chain...
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