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Related Concept Videos

Physical Properties of Carboxylic Acid Derivatives01:19

Physical Properties of Carboxylic Acid Derivatives

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Intermolecular forces dictate several physical properties such as boiling points, melting points, solubilities, and so forth. They are classified into four types: ionic forces, hydrogen bonds, dipole–dipole forces, and dispersion forces. Ionic forces are the strongest, while dispersion forces are the weakest.
Among the carboxylic acid derivatives, the boiling points of acid chlorides and esters are very similar and are the lowest in the series. Acid anhydrides have slightly higher boiling...
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Physical Properties of Ethers02:17

Physical Properties of Ethers

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Overview
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols. Ethers are considered...
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Types of Enols and Enolates01:19

Types of Enols and Enolates

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Aldehydes and ketones form enols, although only about 1% of the enol is present at the equilibrium for simple monocarbonyl compounds. The enol form is undetectable for acetaldehyde, present as only 1.5 × 10−4 % of acetone, and present as only 1.2% of cyclohexanone. Two kinds of regioisomeric enols are possible for unsymmetrical ketones, and their net composition is 1% at equilibrium. This instability is due to the lower bond energy of C=C than the C=O group. The additional...
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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

3.0K
Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

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The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

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Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
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Covalent Attachment of Single Molecules for AFM-based Force Spectroscopy
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Covalent Attachment of Single Molecules for AFM-based Force Spectroscopy

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Ester Bond: Chemically Labile Yet Mechanically Stable.

Hai Lei1,2,3, Quan Ma4, Zhangxia Wang5

  • 1Collaborative Innovation Center of Advanced Microstructures, National Laboratory of Solid State Microstructure, Department of Physics, Nanjing University, Nanjing 210093, China.

ACS Nano
|August 30, 2023
PubMed
Summary

Ester bonds are chemically labile but mechanically stable. This study shows ester hydrolysis is insensitive to mechanical forces, suggesting their use as inert units in responsive materials.

Keywords:
atomic force microscopyester bondhydrolysismechanical forceprotein unfoldingsingle-molecule force spectroscopy

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Area of Science:

  • Chemical Engineering
  • Materials Science
  • Biochemistry

Background:

  • Ester bonds enable material degradability and responsiveness.
  • The influence of mechanical forces on ester hydrolysis is not well understood.

Purpose of the Study:

  • To investigate the force-dependent hydrolysis of ester bonds.
  • To determine if mechanical forces impact ester bond stability.

Main Methods:

  • Developed a single-molecule assay using engineered proteins with caged ester bonds.
  • Utilized single-molecule force spectroscopy to measure hydrolysis rates.
  • Performed quantum calculations to understand hydrolysis mechanisms.

Main Results:

  • Ester hydrolysis rate is largely insensitive to applied forces (80-200 pN).
  • Dissociation rate remains constant at approximately 7 s⁻¹ across tested forces.
  • Quantum calculations suggest the rate-limiting step is also force-insensitive.

Conclusions:

  • Ester bonds are mechanically stable despite being chemically labile.
  • This mechanical stability allows for the design of responsive materials using ester bonds as inert components.