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Related Concept Videos

Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
Oxidation and Reduction of Organic Molecules01:19

Oxidation and Reduction of Organic Molecules

Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
The removal of an electron from a molecule, results in a...
Protecting Groups for Aldehydes and Ketones: Introduction01:23

Protecting Groups for Aldehydes and Ketones: Introduction

Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives01:18

Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives

Aldehydes are more reactive than carboxylic acids and hence, can get over-reduced to alcohol in the presence of strong reducing agents. Therefore, carboxylic acids are inefficient in preparing aldehydes using LAH.
Carboxylic acid derivatives like acid chlorides and esters are more easily reducible than the corresponding acids. The derivatives reduce in the presence of mild reducing agents to give aldehydes. Aldehydes can also be prepared by Rosenmund reduction, that is, the reduction of acid...
Phase I Reactions: Reductive Reactions01:27

Phase I Reactions: Reductive Reactions

Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...
Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids01:24

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H] allows...

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Rapid in-silico Battery Electrolyte Electrochemical Reaction Generation using 3T-VASP Multi-Scale Energy Minimization
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Efficient computational methods for accurately predicting reduction potentials of organic molecules.

Amy L Speelman1, Jason G Gillmore

  • 1Department of Chemistry, Hope College, 35 E. 12th St., Holland, Michigan 49422-9000, USA.

The Journal of Physical Chemistry. A
|June 21, 2008
PubMed
Summary

This study presents a straightforward computational method for predicting reduction potentials of organic molecules. The approach accurately estimates electron affinity using density functional theory, simplifying complex electrochemical predictions.

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Area of Science:

  • Computational Chemistry
  • Electrochemistry
  • Organic Photochemistry

Background:

  • Accurate prediction of ground-state reduction potentials is crucial for understanding and designing organic photooxidants.
  • Existing computational methods can be computationally expensive, limiting their widespread application.

Purpose of the Study:

  • To develop a simple and efficient computational approach for predicting ground-state reduction potentials of organic molecules.
  • To validate the method's accuracy using a diverse set of organic photooxidants.

Main Methods:

  • Gas phase geometry optimizations using moderate-level density functional theory (DFT).
  • Single-point energy calculations at higher DFT levels in gas phase or with polarizable continuum solvent models (IPCM, CPCM).
  • Computation of D0 - S0 energy differences (electron affinity) for 35 planar aromatic organic molecules.

Main Results:

  • High correlations (r(2) > 0.97) between computed electron affinity and experimental reduction potentials were achieved.
  • Residuals were approximately 100 mV or less, demonstrating excellent predictive accuracy.
  • The method proved effective both in gas phase and with implicit solvent models.

Conclusions:

  • The described computational approach offers a simple, accurate, and efficient alternative for predicting reduction potentials.
  • This method avoids computationally intensive vibrational calculations and thermodynamic cycles.
  • The findings facilitate the design and study of organic photooxidants without extensive experimental or computational resources.