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Related Concept Videos

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

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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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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

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Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
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Acid Halides to Amides: Aminolysis01:07

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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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Acids, Bases and Neutralization Reactions03:26

Acids, Bases and Neutralization Reactions

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An acid-base reaction is one in which a hydrogen ion, H+, is transferred from one chemical species to another. Such reactions are of central importance to numerous natural and technological processes, ranging from the chemical transformations within cells or lakes and oceans to the industrial-scale production of fertilizers, pharmaceuticals, and other substances essential to the society.
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Acids, Bases and Neutralization Reactions01:27

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Acids and bases play several important roles in biology. The pH of a biological system can significantly impact the function of biological molecules, including enzymes, proteins, and nucleic acids. For example, enzymes have optimal pH ranges for their activity, and changes in pH can denature or alter their structure, affecting their function. Acids and bases also play a crucial role in cellular signaling and communication. The pH of the extracellular fluid around cells can influence the...
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Repeatable Perming via Thiol-Michael Click Reaction: Using Amide Derived from Maleic Acid and Cystine.

Zezhi Liu1, Ling Ma1,2, Timson Chen2

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|January 28, 2026
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Summary

This study introduces a novel molecule for repeatable hair perming without oxidative damage. The new method offers comparable results to traditional perming while preserving hair integrity over multiple cycles.

Keywords:
disulfide bondhair keratin fiberhair permingoxidative damagethiol–Michael

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Area of Science:

  • Cosmetic Science
  • Materials Science
  • Biochemistry

Background:

  • Conventional hair perming uses oxidative agents, causing significant hair damage.
  • Existing thiol-Michael click perming methods avoid oxidative damage but lack repeatability.

Purpose of the Study:

  • To develop a novel thiol-Michael click perming molecule for repeatable applications without oxidative damage.
  • To evaluate the efficacy, safety, and hair-preserving qualities of the new perming strategy.

Main Methods:

  • Synthesis and characterization of N,N'-bis(maleoyl)-l-cystine (MA2-CySS) using Raman spectroscopy and 1H NMR.
  • Cytotoxicity assessment via MTT assay.
  • Click reactivity analysis under varying pH and temperature conditions.
  • Evaluation of perming efficiency, color change, cuticle damage (SEM), mechanical properties, and keratin structure preservation (Raman spectroscopy).

Main Results:

  • MA2-CySS demonstrated no cytotoxicity up to 1000 μg/mL.
  • The thiol-Michael click reaction reached completion within 30 minutes, with optimal reactivity at alkaline pH and elevated temperatures.
  • MA2-CySS perming achieved high efficiency over three cycles, comparable to oxidative perming.
  • The method significantly reduced hair color change and cuticle damage while maintaining superior mechanical properties.
  • Raman spectroscopy confirmed better preservation of hair keratin's secondary structure, higher alpha-helix content, disulfide bond retention, and favorable conformational changes compared to oxidative perming.

Conclusions:

  • Repeatable hair perming without oxidative damage is achievable using the novel MA2-CySS molecule via thiol-Michael click chemistry.
  • This innovative approach offers a safer and more effective alternative to conventional perming methods, preserving hair quality.
  • The findings represent a significant advancement in hair perming technology, enhancing both performance and hair health.