Compiled by dr. Péter Mátyus

Development of Complex Curricula for Molecular Bionics and Infobionics Programs within a consortial* framework**

Consortium leader

PETER PAZMANY CATHOLIC UNIVERSITY

Consortium members

SEMMELWEIS UNIVERSITY, DIALOG CAMPUS PUBLISHER

The Project has been realised with the support of the European Union and has been co-financed by the European Social Fund ***

**Molekuláris bionika és Infobionika Szakok tananyagának komplex fejlesztése konzorciumi keretben

***A projekt az Európai Unió támogatásával, az Európai Szociális Alap társfinanszírozásával valósul meg.

Organic and Biochemistry

Nomenclature of organic compounds advanced

(Szerves és Biokémia )

(Szerves vegyületek nómenklatúrája haladóknak)

Compiled by dr. Péter Mátyus

with contribution by dr. Gábor Krajsovszky

Formatted by dr. Balázs Balogh

1. Substitutive name 4 – 6

2. Choice for principal chain 7 – 11

3. Selection rules of the ring systems 12 – 15 4. Priority order of functional groups 16 – 19

5. Prefixes 20 – 22

6. Numbering principles 23 – 24

SUBSTITUTIVE name:

The most important names, that are recommended by IUPAC.

Substitutive name indicates the exchange of one or more hydrogen atoms attached to a skeletal atom of a parent structure, which may be expressed by a suffix or by prefixes.

The parent chain or ring (system) is such a linear chain without branching or cyclic structure, or such an acyclic or cyclic structure with a semisystematic or trivial name, which has only hydrogen atoms attached and does not contain any functional groups.

If the main skeleton is linear, than this should be chosen as parent chain, if it is cyclic, then the ring of the highest priority would make the parent ring.

Choice for principal chain/ring:

1. If the compound has only chain, the principal chain is the chain with the highest priority / see later /

2. If the compound has only rings, the principal ring is the ring with the highest priority /see later /

2,3,3-trimethylpentane

1-phenylnaphthalene

C

3

CH₃ CH

2

CH₃ C

H₃

1

CH₃ CH₂

4

CH₃

5

3. If there are both chains and rings, the principal chain (ring) is that contains a) the maximum number of principal groups

b) the maximum number of side chains and/or cyclic groups 1-phenylbutan-2-one

4,5-dichloro-2-(4-carboxybutyl)- -1-cyclohexanecarboxylic acid

C

2

O CH₂

1

CH₂

3

CH₃

4

CH₂

3

CH₂

2

CH₂

1

CH₂

4

COOH

5 2

5 1 4

COOH Cl

Cl

Choice for principal chain:

(The following criteria are applied successively, in the order listed, until a decision is reached.)

1. Maximum number of substituents corresponding to the principal group:

2-(2-bromo-ethyl)butane-1,4-diol 2. The maximum number of multiple bonds (double and triple bonds

considered together):

5-(but-1-en-1-yl)nona- -3,5-diene-1,7-diyne

OH CH₂

1

CH

2

CH₂ CH₂

3

CH₂

4

CH₂ O

H

Br

CH CH

C

5

CH

6

CH

4

CH

3

C

7

C

2

C

8

C H

1

C H₃

9 CH₂ CH₃

3. Maximum lenght:

4. Maximum number of double bonds:

5. Lowest locants for the principal groups (that is, for the suffix):

4-ethylheptane

4-(prop-1-yn-1-yl)- hepta-1,5-diene

4-(2-hydroxypropyl) heptane-1,5-diol

CH₂

6

CH₂

5

CH

4

CH₂ CH₂

3

CH₂

2

C H₃ C

H₃

1

CH₃

7

CH

2

CH₂

3

CH

4

C CH

5

CH

6

C C H₃

7

CH₂

1

C H₃

CH₂

2

CH₂

3

CH

4

CH₂ CH

5

CH₂

6

CH C

H₃

7

CH₂

1

C H₃

OH

OH

6. Lowest locants for multiple bonds (double or triple bonds):

7. Lowest locants for double bonds:

5-(but-2-yn-1-yl)non-1-en-6-yne

6-(pent-3-en-1-yn-1-yl)undeca-1,4,7-trien-9-yne

CH₂

3

CH₂

4

CH

5

CH₂ C

6

C

7

C C H₂

8

CH

2

C C

H₃

9

CH₂

1

C H₃

CH

4

CH

5

CH

6

CH

7

C C

CH

8

C H

CH₂

3

C

9

C H

CH

2

C

10 CH₂

1

C H₃

C H₃

11

8. Maximum number of substituents cited as prefixes:

3-chloro-2,5,6-trimethyl-4- -(2-methylpropyl)-1-nitrohep-tane

9. Lowest locants for all substituents cited as prefixes:

4-(2-ethylbutyl)-5- methyloctanenitrile

CH

2

CH

3

CH

4

CH₂ CH

5

CH

6

C H C H₃

7

CH₂

1

C H₃

CH₃ CH₃

Cl CH₃ NO₂ CH₃

CH₂

2

CH₂

3

CH

4

CH

5

CH₂ CH

CH₂

6

CH₂

C

1

CH₂

7

C H₃

C H₃

8 N

CH₃ CH₂ CH₃

10. The substituent (prefix) first cited in alphabetical order:

6-bromo-4-(2-chloropropyl) heptan-2-ol

11. Lowest locants for the substituent cited first as prefix in alphabetical order:

5-bromo-4-(2-bromo-1-chloropropyl)- -6-chloroheptanoic acid

CH

2

CH₂

3

CH

4

CH₂

5

CH₂ CH

C H

6

C H₃

CH₃

1

C H₃

7

Cl

OH Br

CH₂

2

CH₂

3

CH

4

CH CH

5

CH

6

C H C H₃

7

C

1

C H₃

Br Cl

Br

OH O

Cl

(The following criteria are applied successively, in the order listed, until a decision is reached.)

1. Ring system with largest number of rings:

2. Ring system with largest individual ring at first point of difference:

3. Ring system with largest number of atoms in common among rings:

>

>

> >

expression for ring junctions:

5. Ring system with lowest numbers at the first point of difference in the expression for ring junction:

6. Ring system with lowest state of hydrogenation:

>

1 2

N

1 2

N

f f

e e

d d

c c

b b

a

a

>

1 2

N

f f

e

e d

d c

c b

b a

a

1 2

N

1,2-f 2,1-f

> >

a) indicated hydrogen:

b) point of attachment:

c) an attached group expressed as suffix:

>

N H

1

3

N1 2

>

N 2

3

N

2

>

N H

O

4

N H O

e) that substituent named as prefix which is cited first in the name (according to alphabetical order):

d) substituents named as prefixes, hydro prefixes, -ene, and –yne, all considered together in one series in ascending numerical order:

2

>

1

CH₃ Cl

2 3

Cl

CH₃

3

>

2 4

N₁ NO₂

Cl

3 2 4

N₁ Cl

NO₂

1. Functional groups cited only as prefixes:

functional group prefix

-Br Bromo

-Cl Chloro

-ClO Chlorosyl

-ClO₂ Chloryl

-ClO₃ Perchloryl

-F Fluoro

-I Iodo

=N₂ Diazo

-N₃ Azido

-NO Nitroso

-NO₂ Nitro

-OR Alkyl-oxy

-SR Alkyl-sulfanyl

2. Functional groups that can be cited as prefixes as well as suffixes

a) The following order of functional groups is the decreasing order of priority.

b) The functional group with the highest priority would be the principal group, cited as suffix

c) One kind of principal group should be chosen, but there might be more of the same kind of, in that case, multiplying prefixes should be used ( di-, tri-, etc..).

d) Other functional groups must be cited as prefixes in alphabetic order

ammonio ammonium

cations diazonio diazonium

oxonio oxonium

acids

carboxy carboxylic acid sulfo sulfonic acid

carboxylic acid derivatives

- anhydride

R-oxy-carbonyl R-yl….oate (C), R-yl carboxylate carbamoyl (carbox)amide

O

O H

S O

O O H

N H₃ ⁺

N⁺ N

O H₂ ⁺

C O O

C O

O C O C

H₃

O

carboxylic acid derivatives

sulfamoyl sulfonamide cyano nitrile (C),

carbonitrile

oxo compounds formyl al(C),

carbaldehyde

oxo on

alcohols, phenols, thiols,

arylthiols

hydroxy ol

sulfanyl thiol

amines imines

amino imino

amine imine

S O

O N H₂

N C

O

H

O

H S H O

N N

N H H₂

N H

a) Non-detachable prefixes (nor-, homo-, hydro-, seko-, cyclo-, iso-, anhydro-, desmethyl-, etc...) are immediately preceded the name; e.g., tetrahydronaphthalene.

b) Detachable prefixes must be cited as prefixes and alphabetized before non-detachable prefixes. They have two subtypes:

- Simple prefix (i.e. those describing atoms and unsubstituted substituents) are arranged alphabetically; multiplying affixes are then inserted and do not alter the alphabetical order alredy established. Multiplying affixes are the following: di-, tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, etc… .

- The name of a prefix for a substituted substituent is considered to begin with the first letter of its complete name. Multiplying affixes (bis-, tris-, tetrakis-, etc.) are then inserted and do not alter the alphabetical order alredy established.

3,5,5-tris(1-methylethyl)octane

C

H₃ CH₂ CH CH₂ C CH₂ CH₂ CH HC

CH

CH₃ CH₃

CH₃

C

H₃ CH₃ CH₃

C H₃

1. Multiplying affix (at simple prefixes) does not alter the alphabetical order alredy established.

2. Prefixes are cited in alphabetic order.

2,2,5-trichloro-4,4-dimethylheptane

2,2-dimethylpropyl-

C

H₃ C CH₂ C CH CH₂ Cl CH₃

CH₃

CH₃

Cl Cl

3. Multiplying affix alters the alphabetic order at composited prefixes.

C CH₂ C

H₃

CH₃

CH₃

5. ortho-, meta-, and para- Substituted substituents, if otherwise identical, are arranged in that order (the same as that of their numerical equivalents, 2-, 3-, and 4-, respectively).

for citation is given to that radical which contains the lowest locant at the first-cited point of difference.

3-(1-bromoethyl)-

1-(2-bromoethyl)naphthalene

4-(o-chlorophenyl)- 2-(p-chlorophenyl)pyridine

CH₂ CH₂ Br

CH Br

CH₃

2 1 3

4

2

3

1N

4

6 5

1

Cl Cl 2

The lowest locants must be given for 1. Indicated hydrogen

2. Principal group

3. Double, then the triple bonds 4. Every prefixes

5. The locants for the prefixes cited first in alphabetic order

2-cyclohex-2-en-1-ol

3,4-dichlorocyclohex-1-ene

1-methyl-4-nitronaphthalene

2 3 1

4

NO₂ CH₃

3 2

4

1

Cl Cl

1 2 3

OH

1. For rings, the attachment gets the lowest locants; fused rings according to the numbering rules

4-nitrophenyl

4-nitronaphth-2-yl

2,2-dimethylpropyl

2. For aliphatic side chains, the attachment gets always the locant 1

C CH₂ C

H₃

CH₃

CH₃ NO₂

2 3 1

4

NO₂