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Related Concept Videos

NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

8.7K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
8.7K
NMR Spectroscopy of Aromatic Compounds01:14

NMR Spectroscopy of Aromatic Compounds

4.9K
Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range.
4.9K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

11.1K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
11.1K
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

8.5K
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).
8.5K
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

1.9K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
1.9K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.9K
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...
2.9K

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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1,4-Bis-(4-meth-oxy-phen-yl)naphthalene.

R Manickam1, G Jagadeesan2, J Karunakaran3

  • 1PG and Research Department of Physics, Government Arts College for Men (Autonomous), Nandanam, Chennai - 600 035, India.

Iucrdata
|November 7, 2022
PubMed
Summary
This summary is machine-generated.

This study details a novel naphthalene derivative (C24H20O2) with specific methoxy-substituted benzene rings. Molecular analysis reveals similar conformations and crystal packing stabilized by C-H⋯π interactions, forming supramolecular chains.

Keywords:
C—H⋯π inter­actionscrystal structurenaphthalene derivative

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Materials Science

Background:

  • Naphthalene derivatives are important in various chemical applications.
  • Understanding molecular conformation and crystal packing is crucial for material properties.

Purpose of the Study:

  • To characterize the crystal structure and molecular conformation of a novel naphthalene derivative.
  • To investigate the intermolecular interactions and supramolecular assembly in the crystal.

Main Methods:

  • Single-crystal X-ray diffraction was used to determine the molecular structure.
  • Analysis of bond lengths, angles, and dihedral angles provided conformational insights.
  • Identification of intermolecular interactions (C-H⋯π) and packing motifs.

Main Results:

  • Two independent molecules (A and B) with similar conformations were identified.
  • Naphthalene cores showed slight bending, with dihedral angles between benzene rings of ~3-4°.
  • Methoxybenzene rings were splayed out at dihedral angles of ~60-67°.
  • Intermolecular C-H⋯π interactions formed supramolecular chains along the b-axis.

Conclusions:

  • The study provides a detailed structural characterization of the title naphthalene derivative.
  • The observed molecular conformation and crystal packing are influenced by C-H⋯π interactions.
  • The formation of supramolecular chains suggests potential for ordered material assembly.