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The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for symmetrical secondary and tertiary amines, prefixes di- and tri- are used, respectively. On the other hand, in the case of unsymmetrical amines, individual substituents are identified and listed alphabetically.

Figure1

Figure 1. The nomenclature of symmetric and asymmetric secondary and tertiary amines.

In the IUPAC nomenclature, the secondary and tertiary amines are named N-alkylalkanamines. The IUPAC name for a structure is assigned via the following protocol:

  1. First, identify the alkyl groups attached to the nitrogen atom.
  2. Next, select the longest chain as the parent, while other alkyl groups are listed as substituents. While numbering the parent hydrocarbon chain, assign the lowest number to the carbon atom bearing nitrogen atom.
  3. Then, assign locants to each substituent. Use the letter N as the locant for the alkyl groups attached to the nitrogen atom.
  4. Finally, specify the configuration of the chiral center at the beginning of the name, if any is present.

Two examples of the above are illustrated in Figure 2.

Figure2

Figure 2. The IUPAC names of two example amines.

IUPAC names for quaternary ammonium ions are assigned by naming them as secondary and tertiary amines. However, the suffix -amine is replaced with -ammonium, followed by the name of counterion, as depicted in Figure 3.

Figure3

Figure 3. The IUPAC names of various quaternary amines.

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Secondary AminesTertiary AminesAlkyl GroupsNomenclatureSymmetrical AminesUnsymmetrical AminesIUPAC NomenclatureN alkylalkanaminesLocantsChiral CenterQuaternary Ammonium Ions

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19.3 : Nomenclature of Secondary and Tertiary Amines

アミン

3.5K 閲覧数

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19.1 : アミン:はじめに

アミン

4.0K 閲覧数

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19.2 : 第一級アミンの命名法

アミン

3.2K 閲覧数

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19.4 : アリールおよび複素環式アミンの命名法

アミン

2.2K 閲覧数

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19.5 : アミンの構造

アミン

2.4K 閲覧数

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19.6 : アミンの物性

アミン

2.8K 閲覧数

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19.7 : 脂肪族アミンの塩基性

アミン

5.6K 閲覧数

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19.8 : 芳香族アミンの塩基性

アミン

6.9K 閲覧数

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19.9 : 複素環芳香族アミンの塩基性

アミン

5.3K 閲覧数

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19.10 : アミンのNMR分光法

アミン

8.1K 閲覧数

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19.11 : アミンの質量分析

アミン

4.0K 閲覧数

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19.12 : アミンの調製:アンモニアとアミンのアルキル化

アミン

3.1K 閲覧数

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19.13 : 1°アミンの調製:アジド合成

アミン

3.7K 閲覧数

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19.14 : 1°アミンの調製:ガブリエル合成

アミン

3.4K 閲覧数

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19.15 : アミンの調製:オキシムおよびニトロ化合物の還元

アミン

3.2K 閲覧数

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