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

Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated benzene...
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...

You might also read

Related Articles

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

Sort by
Same author

Diagnosing conformational preferences of lower-rim-functionalized thiophene resorcin[4]arenes and pyrogallol[4]arenes for predictable supramolecular assembly design.

Physical chemistry chemical physics : PCCP·2026
Same author

Acute Small Bowel Obstruction Induced by Tirzepatide (Mounjaro).

Cureus·2026
Same author

Methane storage using metal-dipyrazolate frameworks.

Nature materials·2026
Same author

Healing crystals without heat.

Nature materials·2025
Same author

The Chemistry of Space: From Crystallographic Abstraction to Framework Design.

Angewandte Chemie (International ed. in English)·2025
Same author

Inflatable porous organic crystals.

Nature materials·2025

Related Experiment Video

Updated: May 7, 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

Pyrogallol[4]arenes as frustrated organic solids.

Harshita Kumari1, Loredana Erra, Alicia C Webb

  • 1Department of Chemistry, University of Missouri-Columbia , 601 S. College Avenue, Columbia, Missouri 65211, United States.

Journal of the American Chemical Society
|September 18, 2013
PubMed
Summary

Researchers studied C-pentylpyrogallol[4]arene (PgC5) and found seven forms, including CO2 interactions. Pyrogallol[4]arenes show potential as frustrated organic solids, impacting materials science.

More Related Videos

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
09:46

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

Published on: August 19, 2013

Related Experiment Videos

Last Updated: May 7, 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

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
09:46

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

Published on: August 19, 2013

Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Solid-State Chemistry

Background:

  • Interdigitated layered structures are crucial in supramolecular chemistry.
  • Pyrogallol[4]arenes are a class of compounds with potential applications in gas storage.
  • Understanding their solid-state behavior and guest interactions is key to developing new materials.

Purpose of the Study:

  • To elucidate the structural variations in C-pentylpyrogallol[4]arene (PgC5) layered arrangements.
  • To investigate the host-guest interactions, particularly with CO2.
  • To explore the potential of pyrogallol[4]arenes as frustrated organic solids.

Main Methods:

  • X-ray Powder Diffraction (PXRD) to analyze solid-state structures.
  • Gas sorption techniques to study CO2 uptake and interactions.
  • Molecular dynamics simulations to understand molecular arrangements and self-assembly.

Main Results:

  • Two distinct interdigitated layered arrangements of PgC5 were structurally characterized.
  • Molecular dynamics revealed the formation of self-included dimers, with or without solvent.
  • Seven forms of PgC5, with and without CO2, were identified through gas sorption and PXRD, including interconversions.

Conclusions:

  • Pyrogallol[4]arenes exhibit diverse solid-state forms and packing arrangements.
  • The study provides the first evidence of CO2 sorption in pyrogallol[4]arenes.
  • Pyrogallol[4]arenes demonstrate characteristics of frustrated organic solids, opening avenues for new material design.