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

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...

You might also read

Related Articles

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

Sort by
Same author

Credible Mendelian Randomization Studies in the Presence of Selection Bias Using Control Exposures.

Frontiers in genetics·2021
Same author

Construction of an enzyme-based all-fiber SPR biosensor for detection of enantiomers.

Biosensors & bioelectronics·2021
Same author

Performance improvement-oriented reentry attitude control for reusable launch vehicles with overload constraint.

ISA transactions·2021
Same author

Polysulfide Catalytic Materials for Fast-Kinetic Metal-Sulfur Batteries: Principles and Active Centers.

Advanced science (Weinheim, Baden-Wurttemberg, Germany)·2021
Same author

Application of post-combustion ultra-low NO<sub>x</sub> emissions technology on coal slime solid waste circulating fluidized bed boilers.

Waste management (New York, N.Y.)·2021
Same author

Activation of PTH1R alleviates epididymitis and orchitis through Gq and β-arrestin-1 pathways.

Proceedings of the National Academy of Sciences of the United States of America·2021

Related Experiment Video

Updated: Jun 1, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

Phenyl N-(4-fluorophen-yl)carbamate.

Zhao Yang1, Zhi-Xiang Wang

  • 1Department of Pharmaceutical Engineering, China Pharmaceutical University, Tongjiaxiang No. 24 Nanjing, Nanjing 210009, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study details the crystal structure of a fluorinated organic compound, C(13)H(10)FNO(2). It reveals two independent molecules linked by N-H⋯O hydrogen bonds, forming crystal chains with weak C-H⋯π interactions.

More Related Videos

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Related Experiment Videos

Last Updated: Jun 1, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding the molecular arrangement and intermolecular forces is crucial for predicting material properties.
  • Crystal structure analysis provides fundamental insights into chemical bonding and supramolecular assembly.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(13)H(10)FNO(2).
  • To identify and characterize the intermolecular interactions present in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of the crystallographic data identified hydrogen bonding and C-H⋯π interactions.

Main Results:

  • The asymmetric unit contains two crystallographically independent molecules of C(13)H(10)FNO(2).
  • The dihedral angles between aromatic rings in the two molecules are 61.77(3)° and 53.94(3)°.
  • Intra- and intermolecular N-H⋯O hydrogen bonds were observed, leading to the formation of molecular chains.
  • Weak C-H⋯π interactions were also identified as a contributing factor to the crystal packing.

Conclusions:

  • The crystal structure of C(13)H(10)FNO(2) is characterized by the presence of two independent molecules and significant intermolecular N-H⋯O hydrogen bonding.
  • These interactions dictate the formation of one-dimensional chains within the crystal lattice.
  • The study provides a detailed understanding of the solid-state structure and intermolecular forces governing this fluorinated organic compound.