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

Directing Effect of Substituents: meta-Directing Groups01:09

Directing Effect of Substituents: meta-Directing Groups

5.9K
Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are called meta directors. All meta directors either have a positive charge on the atom directly bonded to the ring or a partial positive charge. These groups function by withdrawing electrons from the ring through inductive and resonance effects. Consider the carbocation intermediates formed upon the addition of an electrophile on nitrobenzene at the...
5.9K
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

10.1K
In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
10.1K
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

10.2K
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
10.2K
Directing Effect of Substituents: ortho–para-Directing Groups01:14

Directing Effect of Substituents: ortho–para-Directing Groups

8.4K
Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered ortho–para directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate...
8.4K
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

10.4K
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
10.4K
Substituent Effects on Acidity of Carboxylic Acids01:31

Substituent Effects on Acidity of Carboxylic Acids

7.9K
The acidity of carboxylic acids is influenced by the nature of the substituents bounded to the functional group. The acid strength is determined by the stability of the carboxylate anion—the conjugate base formed by dissociating the corresponding carboxylic acid.
7.9K

You might also read

Related Articles

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

Sort by
Same author

Chemical Transformations of Benzyl Alcohol Caused by Atomic Chlorine.

Molecules (Basel, Switzerland)·2024
Same author

What Is the Main Feature Distinguishing the Through-Space Interactions in Cyclophanes from Their Aliphatic Analogues?

ACS omega·2020
Same author

Aromaticity and Electron Density of Hypericin.

Journal of natural products·2019
Same author

Aromaticity of benzene derivatives: an exploration of the Cambridge Structural Database.

Acta crystallographica Section B, Structural science, crystal engineering and materials·2018
Same author

Aromaticity of peri- and para-Substituted Naphthalene-1-carbaldehyde. Comparison with 1-Nitronaphthalene.

The journal of physical chemistry. A·2017
Same author

Aromaticity and Through-Space Interaction between Aromatic Rings in [2.2]Paracyclophanes.

The journal of physical chemistry. A·2016

Related Experiment Video

Updated: Jan 28, 2026

How to Calculate and Validate Inter-brain Synchronization in a fNIRS Hyperscanning Study
05:33

How to Calculate and Validate Inter-brain Synchronization in a fNIRS Hyperscanning Study

Published on: September 8, 2021

7.4K

Substituent effect on inter-ring interaction in paracyclophanes.

Irena Majerz1, Teresa Dziembowska2

  • 1Faculty of Pharmacy, Wroclaw Medical University, Borowska 211a, 50-556, Wrocław, Poland. majerz@yahoo.com.

Molecular Diversity
|February 21, 2019
PubMed
Summary
This summary is machine-generated.

Theoretical calculations reveal substituent effects and bridge length influence aromatic ring interaction energy and strain in paracyclophanes. Weak C···C and CH···O interactions were observed.

Keywords:
AIENCISE[2.2]Paracyclophane[2.2]Paracyclophane-7,9-dienes[3.3]Paracyclophanes QTAIM

More Related Videos

Inter-Brain Synchrony in Open-Ended Collaborative Learning: An fNIRS-Hyperscanning Study
04:44

Inter-Brain Synchrony in Open-Ended Collaborative Learning: An fNIRS-Hyperscanning Study

Published on: July 21, 2021

4.9K
Determination of Self- and Inter-incompatibility Relationships in Apricot Combining Hand-Pollination, Microscopy and Genetic Analyses
08:08

Determination of Self- and Inter-incompatibility Relationships in Apricot Combining Hand-Pollination, Microscopy and Genetic Analyses

Published on: June 16, 2020

7.8K

Related Experiment Videos

Last Updated: Jan 28, 2026

How to Calculate and Validate Inter-brain Synchronization in a fNIRS Hyperscanning Study
05:33

How to Calculate and Validate Inter-brain Synchronization in a fNIRS Hyperscanning Study

Published on: September 8, 2021

7.4K
Inter-Brain Synchrony in Open-Ended Collaborative Learning: An fNIRS-Hyperscanning Study
04:44

Inter-Brain Synchrony in Open-Ended Collaborative Learning: An fNIRS-Hyperscanning Study

Published on: July 21, 2021

4.9K
Determination of Self- and Inter-incompatibility Relationships in Apricot Combining Hand-Pollination, Microscopy and Genetic Analyses
08:08

Determination of Self- and Inter-incompatibility Relationships in Apricot Combining Hand-Pollination, Microscopy and Genetic Analyses

Published on: June 16, 2020

7.8K

Area of Science:

  • Computational chemistry
  • Organic chemistry
  • Molecular modeling

Background:

  • Paracyclophanes are unique cyclic molecules with interacting aromatic rings.
  • Understanding substituent and structural effects is crucial for predicting their properties.

Purpose of the Study:

  • To investigate the substituent effects of electron-donating and withdrawing groups on paracyclophane systems.
  • To analyze the impact of bridge length on aromatic ring interaction energy (AIE) and strain energy.
  • To elucidate the nature of intermolecular interactions within these systems.

Main Methods:

  • Advanced theoretical calculations including multipole-derived charge analysis, quantum theory of atoms in molecules (QTAIM), and non-bonding interaction (NBI) analysis.
  • Geometry optimization of various paracyclophane derivatives using the B3LYP/6-311++G** level of theory with dispersion correction.

Main Results:

  • The study demonstrated the local and electrostatic nature of substituent effects in paracyclophanes.
  • Aromatic ring interaction energy (AIE) and strain energy were found to be significantly influenced by substituent type and bridge length.
  • Weak through-space C···C orbital interactions in [3.3]paracyclophanes and CH···O hydrogen bonds between substituents were identified.

Conclusions:

  • Substituent groups and bridge length play critical roles in modulating the electronic structure and stability of paracyclophanes.
  • The findings provide insights into the non-covalent interactions governing the behavior of these complex organic molecules.
  • This research contributes to a deeper understanding of structure-property relationships in cyclophane chemistry.