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

UV–Vis Spectroscopy: Woodward–Fieser Rules01:29

UV–Vis Spectroscopy: Woodward–Fieser Rules

UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the contributions...
Experimental Determination of Chemical Formula02:37

Experimental Determination of Chemical Formula

The elemental makeup of a compound defines its chemical identity, and chemical formulas are the most concise way of representing this elemental makeup. When a compound’s formula is unknown, measuring the mass of its constituent elements is often the first step in determining the formula experimentally.
Indirect-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship01:29

Indirect-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship

Indirect-acting cholinergic agonists are agents that interact with the acetylcholinesterase enzyme in the synaptic cleft, preventing the breakdown of acetylcholine into choline and acetate. Consequently, the concentration of acetylcholine in the synaptic cleft increases. These agonists can be classified into reversible and irreversible inhibitors based on their duration of action.
Reversible inhibitors display short to medium durations of action. Short-acting agents include simple alcohols with...
Inductive Effects on Chemical Shift: Overview01:27

Inductive Effects on Chemical Shift: Overview

The protons in unsubstituted alkanes are strongly shielded with chemical shifts below 1.8 ppm. Methine, methylene, and methyl protons appear at approximately 1.7, 1.2 and 0.7 ppm, while the proton signal from methane appears at 0.23 ppm. An electronegative substituent, such as chlorine, withdraws the electron density from the protons, increasing their chemical shift. Progressive substitution of the hydrogens in methane by chlorine shifts the proton signals increasingly downfield, to 3.05 ppm in...
X-ray Crystallography02:18

X-ray Crystallography

The size of the unit cell and the arrangement of atoms in a crystal may be determined from measurements of the diffraction of X-rays by the crystal, termed X-ray crystallography.
Diffraction
Diffraction is the change in the direction of travel experienced by an electromagnetic wave when it encounters a physical barrier whose dimensions are comparable to those of the wavelength of the light. X-rays are electromagnetic radiation with wavelengths about as long as the distance between neighboring...
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.

You might also read

Related Articles

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

Sort by
Same author

Pressure-induced suppression of supramolecular dynamics in hydrogen-bonded adamantane derivative.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy·2026
Same author

A novel family of heteroleptic 1D chain spin-crossover complexes and its DFT modelling. How the formation of polynuclear chains modifies the ligand-field effects on spin transition.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Quantum Insights into IR Spectral Density of Hydrogen-Bonded Cyclic Dimers: RS-Ibuprofen and RS-Ketoprofen as Model Systems.

The journal of physical chemistry. A·2026
Same author

The Ammann-Kramer-Neri tiling model of a P-ZnMgEr Bergman-type quasicrystal based on in-house X-ray diffraction.

Acta crystallographica Section B, Structural science, crystal engineering and materials·2026
Same author

Pressure-Induced Self-Assembly in 3-Phenylpropanal: Distinct Clustering via π-Stacking and Distorted Hydrogen Bonds.

The journal of physical chemistry letters·2026
Same author

Effect of solvent evaporation on the liquid-crystalline order of itraconazole.

Scientific reports·2025

Related Experiment Video

Updated: May 28, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

6-Chloro-2-oxindole: X-ray and DFT-calculated study.

Barbara Hachuła1, Piotr Zerzucha, Maciej Zubko

  • 1Institute of Chemistry, University of Silesia, 14th Bankowa Street, 40-006 Katowice, Poland. bhachula@o2.pl

Acta Crystallographica. Section C, Crystal Structure Communications
|October 8, 2011
PubMed
Summary

This study reveals the crystal structure of 6-chloroindolin-2-one, detailing its near-planar geometry and hydrogen bonding interactions. Computational analysis confirmed molecular structure and electronic properties, explaining observed spectral shifts.

More Related Videos

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

Related Experiment Videos

Last Updated: May 28, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

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

Area of Science:

  • Crystallography
  • Computational Chemistry
  • Spectroscopy

Background:

  • The crystal structure of 6-chloroindolin-2-one was investigated to understand its molecular geometry and intermolecular interactions.
  • Previous studies may not have fully elucidated the specific bonding and electronic characteristics of this compound.

Purpose of the Study:

  • To determine the precise molecular structure and crystal packing of 6-chloroindolin-2-one.
  • To computationally model the molecule's geometry and electronic properties.
  • To correlate structural findings with spectroscopic data.

Main Methods:

  • X-ray crystallography to analyze the solid-state structure.
  • Density Functional Theory (DFT) calculations using B3LYP/6-31 G(d,p) for structural optimization.
  • Natural Bond Orbital (NBO) analysis for electronic structure.
  • Infrared (IR) spectroscopy to study vibrational properties.

Main Results:

  • The molecule exhibits a nearly planar conformation with a dihedral angle of 1.13° between the pyrrolidine and benzene rings.
  • Centrosymmetric dimers formed via N-H···O hydrogen bonds, with additional Cl···Cl and C-H···O interactions observed.
  • DFT calculations optimized the geometry, best reproduced by considering two interacting molecules.
  • NBO analysis confirmed bond orders consistent with observed lengths, highlighting lone pair contribution to the N-C bond.
  • IR spectroscopy showed a red shift in N-H stretching frequency, indicative of hydrogen bond formation.

Conclusions:

  • The crystal structure of 6-chloroindolin-2-one is characterized by near planarity and specific intermolecular interactions.
  • Computational and spectroscopic methods confirm the electronic structure and the influence of hydrogen bonding on molecular vibrations.