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

Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Inhibitors of Bacterial DNA Synthesis01:28

Inhibitors of Bacterial DNA Synthesis

Bacterial pathogens depend on precise and efficient DNA replication to sustain infection. Two type II topoisomerases—DNA gyrase and topoisomerase IV—are critical to this process, as they resolve DNA supercoiling and unlink chromosomes during replication. Fluoroquinolones, synthetic derivatives of quinolones, exploit this mechanism by stabilizing the transient DNA–enzyme cleavage complex, preventing strand religation, and causing lethal double-strand breaks. These antibiotics are selectively...
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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...
Halogens03:01

Halogens

Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group.
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.

You might also read

Related Articles

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

Sort by
Same author

Structure-Reactivity Relationships in a Small Library of Imine-Type Dynamic Covalent Materials: Determination of Rate and Equilibrium Constants Enables Model Prediction and Validation of a Unique Mechanical Softening in Dynamic Hydrogels.

Journal of the American Chemical Society·2024
Same author

Well-Defined Synthetic Copolymers with Pendant Aldehydes Form Biocompatible Strain-Stiffening Hydrogels and Enable Competitive Ligand Displacement.

Journal of the American Chemical Society·2024
Same author

Michaelis-Menten Quantification of Ligand Signaling Bias Applied to the Promiscuous Vasopressin V2 Receptor.

Molecular pharmacology·2022
Same author

High-throughput Site-directed Scanning Mutagenesis Using a Two-fragment PCR Approach.

Bio-protocol·2021
Same author

Molecular mechanism of leukocidin GH-integrin CD11b/CD18 recognition and species specificity.

Proceedings of the National Academy of Sciences of the United States of America·2019
Same author

Soluble and membrane-bound protein carrier mediate direct copper transport to the ethylene receptor family.

Scientific reports·2019
Same journal

Intermolecular C-H···O, Cl···Cl and π-π interactions in the 2-dichloromethyl derivative of vitamin K3.

Acta crystallographica. Section C, Crystal structure communications·2013
Same journal

Isolation, pharmacological activity and structure determination of physalin B and 5β,6β-epoxyphysalin B isolated from Congolese Physalis angulata L.

Acta crystallographica. Section C, Crystal structure communications·2013
Same journal

Transannular S···N interactions in 10-ethynyl-10H-phenothiazine 5-oxide and 5,5-dioxide.

Acta crystallographica. Section C, Crystal structure communications·2013
Same journal

Two polymorphs of 2-ethyl-3-hydroxy-6-methylpyridinium hydrogen N-acetyl-L-glutamate from powder diffraction data.

Acta crystallographica. Section C, Crystal structure communications·2013
Same journal

Three-dimensional hydrogen-bonded assembly in 2,2'-disulfanylidene-5,5'-biimidazolidinylidene-4,4'-dione-dimethylformamide-water (3/2/4).

Acta crystallographica. Section C, Crystal structure communications·2013
Same journal

Head-to-tail square-shaped cyclic hydrogen bonds leading to dimeric aggregates: 1,8-dibenzoyl-2,7-dihydroxynaphthalene and a comparison with its analogous benzoylnaphthalene.

Acta crystallographica. Section C, Crystal structure communications·2013
See all related articles

Related Experiment Video

Updated: Jun 19, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
11:51

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

Three quinolone compounds featuring O...I halogen bonding.

Jurica Bauer1, Dalibor Milić, Marina Modrić

  • 1GlaxoSmithKline Research Centre Zagreb, Prilaz Baruna Filipovića 29, HR-10000 Zagreb, Croatia.

Acta Crystallographica. Section C, Crystal Structure Communications
|October 7, 2009
PubMed
Summary
This summary is machine-generated.

Three iodoquinolone carboxylates exhibit distinct crystal structures, with O...I halogen bonds forming chains. Intermolecular interactions like C-H...O and pi-pi stacking dictate varied solid-state architectures and molecular arrangements.

More Related Videos

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Green Synthesis of Quinoline-Based Ionic Liquid
05:59

Green Synthesis of Quinoline-Based Ionic Liquid

Published on: September 27, 2024

Related Experiment Videos

Last Updated: Jun 19, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
11:51

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Green Synthesis of Quinoline-Based Ionic Liquid
05:59

Green Synthesis of Quinoline-Based Ionic Liquid

Published on: September 27, 2024

Area of Science:

  • Crystallography and Materials Science
  • Medicinal Chemistry
  • Supramolecular Chemistry

Background:

  • Quinolone derivatives are important pharmaceutical scaffolds.
  • Understanding solid-state structures is crucial for drug development and material properties.
  • Halogen bonding and other non-covalent interactions play significant roles in molecular assembly.

Purpose of the Study:

  • To investigate and compare the crystal structures and supramolecular architectures of three novel ethyl iodoquinolone carboxylate derivatives.
  • To elucidate the role of O...I halogen bonding and other intermolecular forces in dictating the solid-state arrangements.
  • To analyze the relationship between structural variations and molecular planarity.

Main Methods:

  • Single-crystal X-ray diffraction analysis was performed on three ethyl iodoquinolone carboxylate compounds.
  • Crystal structures were analyzed to identify and characterize intermolecular interactions, including halogen bonding (O...I), C-H...O, C-H...pi, and pi-pi stacking.
  • Comparison of crystallographic data and structural features to understand differences in supramolecular assembly.

Main Results:

  • Ethyl 1-ethyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (I) and ethyl 1-cyclopropyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (II) exhibit isomorphous crystal structures.
  • Ethyl 1-dimethylamino-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (III) displays a different supramolecular architecture.
  • In all three compounds, O...I halogen bonds form infinite chains along the b axis.
  • Compounds (I) and (II) feature (101) layers linked by C-H...O interactions, with variations in planarity attributed to differing C-H...O interactions.
  • Compound (III) forms (100) layers crosslinked by O...I and C-H...I interactions.

Conclusions:

  • The solid-state structures of ethyl iodoquinolone carboxylates are significantly influenced by O...I halogen bonding and other non-covalent interactions.
  • Substituent variations at the N1 position lead to distinct supramolecular architectures and affect molecular planarity.
  • The study provides insights into the structure-property relationships of iodoquinolone derivatives, relevant for crystal engineering and drug design.