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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

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Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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Nomenclature of Secondary and Tertiary Amines01:12

Nomenclature of Secondary and Tertiary Amines

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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...
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Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

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Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
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Nomenclature of Alkanes02:22

Nomenclature of Alkanes

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In the late 19th-century, the number of new chemical compounds discovered increased tremendously. Hence, the necessity arose to develop a naming system for the systematic nomenclature of these newly discovered compounds. IUPAC (International Union for Pure and Applied Chemistry), established in 1919, sets rules for the nomenclature.
The alkane nomenclature considers the length of the carbon chain, the number, and the location of the substituent to arrive at its systematic name. The IUPAC...
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IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

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Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic...
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Toward a Systematic Nomenclature for (Neo)Lignanamides.

Annemiek van Zadelhoff1, Wouter J C de Bruijn1, Zhongxiang Fang2

  • 1Laboratory of Food Chemistry, Wageningen University, Bornse Weilanden 9, 6708 WG Wageningen, The Netherlands.

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Summary

A new systematic nomenclature is proposed for phenylalkenoic acid amides, also known as lignanamides. This naming system enhances clarity and consistency for these bioactive phytochemical dimers and oligomers.

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Area of Science:

  • Phytochemistry
  • Natural Products Chemistry
  • Bioorganic Chemistry

Background:

  • Phenylalkenoic acid amides (phenol amides) are bioactive phytochemicals.
  • Their bioactivity can be enhanced through dimerization or oligomerization.
  • These compounds are formed by linking a (hydroxy)cinnamic acid derivative to an amine via an amide bond.

Purpose of the Study:

  • To address the lack of a systematic nomenclature for phenylalkenoic acid amide dimers and oligomers, termed (neo)lignanamides.
  • To propose a new, systematic nomenclature inspired by existing systems for hydroxycinnamic acid dimers and lignin.
  • To ensure consistency, future-proofing, and systematic naming of these compounds.

Main Methods:

  • Reviewing existing literature on phenylalkenoic acid amides and their dimers.
  • Analyzing current naming conventions and their limitations.
  • Developing a new nomenclature based on subunit codes, prefixes, and linkage site indicators.

Main Results:

  • Identified inconsistencies and lack of systematic approach in current naming of (neo)lignanamides.
  • Proposed a new nomenclature system for (neo)lignanamides.
  • The proposed system uses three-letter codes for subunits and numbers for linkage points.

Conclusions:

  • The proposed systematic nomenclature provides a consistent and future-proof method for naming (neo)lignanamides.
  • This new system will improve clarity and facilitate research in the field of bioactive phytochemicals.
  • Implementation of this nomenclature will aid in the systematic study and comparison of these compounds.