Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

5.0K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
5.0K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

10.0K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
10.0K
Phase I Reactions: Reductive Reactions01:27

Phase I Reactions: Reductive Reactions

782
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...
782
Rate-Determining Steps03:08

Rate-Determining Steps

39.7K
Relating Reaction Mechanisms
In a multistep reaction mechanism, one of the elementary steps progresses significantly slower than the others. This slowest step is called the rate-limiting step (or rate-determining step). A reaction cannot proceed faster than its slowest step, and hence, the rate-determining step limits the overall reaction rate.
The concept of rate-determining step can be understood from the analogy of a 4-lane freeway with a short-stretch of traffic-bottleneck caused due to...
39.7K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

7.2K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
7.2K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.3K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
3.3K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Atom-specific vibrational analysis reveals labile bonds in linear and branched PFOA molecules.

The Journal of chemical physics·2026
Same author

A Case for More Diversity in Thinking About PMT Contaminants.

Environmental science & technology·2026
Same author

In Silico Analysis of Contaminant Persistence: From QSARs to Machine Learning Models.

Environmental science & technology·2026
Same author

Interfacial hydrophobicity-induced desolvation effects on reductive dehalogenation by Zero-Valent Iron.

Water research·2026
Same author

<i>ES&T</i> at 60: Science, Community, and the Facets of Impact.

Environmental science & technology·2026
Same author

Nitridated Iron-Based (Nano)Materials for Environmental Remediation: Synthesis, Characterization, and Performance.

Environmental science & technology·2025

Related Experiment Video

Updated: Apr 17, 2026

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
11:44

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds

Published on: October 18, 2018

27.9K

Predicting reduction rates of energetic nitroaromatic compounds using calculated one-electron reduction potentials.

Alexandra J Salter-Blanc, Eric J Bylaska1, Hayley J Johnston

  • 1‡William R. Wiley Environmental Molecular Sciences Laboratory, Pacific Northwest National Laboratory, P.O. Box 999, Richland, Washington 99352, United States.

Environmental Science & Technology
|February 12, 2015
PubMed
Summary

Predicting the environmental fate of nitroaromatic compounds (NACs) is crucial for green munitions. A new quantitative structure-activity relationship (QSAR) accurately models NAC reduction rates, aiding in the development of safer energetic materials.

More Related Videos

Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O
08:05

Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O

Published on: October 7, 2020

6.8K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.8K

Related Experiment Videos

Last Updated: Apr 17, 2026

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
11:44

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds

Published on: October 18, 2018

27.9K
Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O
08:05

Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O

Published on: October 7, 2020

6.8K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.8K

Area of Science:

  • Environmental chemistry
  • Computational chemistry
  • Chemical kinetics

Background:

  • Developing green munitions requires understanding the environmental fate of energetic nitroaromatic compounds (NACs).
  • Existing models based on linear free energy relationships (LFER) for NAC reduction have limitations.
  • Accurate predictive models are needed for environmental risk assessment.

Purpose of the Study:

  • To re-evaluate existing LFER models and develop a new, more accurate quantitative structure-activity relationship (QSAR) for predicting NAC environmental fate.
  • To investigate the applicability of Marcus theory to outer-sphere electron transfer in NAC reduction.
  • To validate the new QSAR model using experimental kinetic data for energetic NACs.

Main Methods:

  • Re-evaluation of linear free energy relationships (LFER) and comparison with nonlinear free-energy relationships (FER) based on Marcus theory.
  • Calibration of a new QSAR using reported and newly determined one-electron reduction potentials (E1NAC) from density functional theory (DFT) calculations.
  • Validation of the QSAR model with newly measured kinetic data for 2,4,6-trinitrotoluene (TNT), 2,4-dinitrotoluene (2,4-DNT), and 2,4-dinitroanisole (DNAN).

Main Results:

  • The linear correlation between log(k) and E1NAC is best considered an empirical model, not solely limited by initial outer-sphere electron transfer.
  • A new QSAR was developed and calibrated using DFT-calculated E1NAC values and experimental reduction rate constants.
  • The validated QSAR showed close agreement with experimental data for energetic NACs, including TNT, 2,4-DNT, and DNAN.

Conclusions:

  • The developed QSAR model accurately predicts the environmental fate of energetic nitroaromatic compounds.
  • The findings support the use of QSAR for assessing the environmental impact of new energetic materials in munitions.
  • This research contributes to the development of greener and safer energetic formulations.