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Related Concept Videos

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...
NMR Spectroscopy of Aromatic Compounds01:14

NMR Spectroscopy of Aromatic Compounds

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. Consider...
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...
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

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 Hückel’s rule or the 4n + 2 rule.
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
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.

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

An aromatic mystery.

James Reid1, Nick Balcombe, Kris Ghosh

  • 1Warwick Hospital, Geriatrics, Lakin Road, Warwick CV34 5BW, UK.

BMJ Case Reports
|February 9, 2012
PubMed
Summary
This summary is machine-generated.

Antiepileptic hypersensitivity syndrome can mimic septic illness. Promptly stopping carbamazepine resolved a patient's severe symptoms, highlighting the importance of considering drug reactions in complex cases.

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Area of Science:

  • Clinical Medicine
  • Pharmacology
  • Neurology

Background:

  • Antiepileptic hypersensitivity syndrome (AHS) is a severe drug reaction.
  • It can present with diverse symptoms, sometimes mimicking infections.
  • Early recognition and drug withdrawal are crucial for patient outcomes.

Purpose of the Study:

  • To report a case of AHS mimicking acute septic illness.
  • To highlight the diagnostic challenges and successful management of this condition.

Main Methods:

  • Case report of a 67-year-old male patient.
  • Initial presentation with pneumonia and periorbital edema, treated with antibiotics.
  • Phenytoin was switched to carbamazepine.
  • Subsequent re-admission with systemic inflammatory symptoms.
  • Extensive investigations for infection, autoimmune disease, and malignancy were negative.
  • Carbamazepine was discontinued, leading to symptom resolution.

Main Results:

  • The patient initially presented with symptoms suggestive of pneumonia and fluid overload.
  • After switching from phenytoin to carbamazepine, the patient developed severe systemic inflammatory symptoms.
  • Discontinuation of carbamazepine led to rapid and complete resolution of all symptoms and normalization of inflammatory markers.
  • No underlying infectious, autoimmune, or malignant cause was identified.

Conclusions:

  • Antiepileptic hypersensitivity syndrome can present as a severe systemic illness, mimicking sepsis.
  • Carbamazepine should be considered as a potential cause in patients with unexplained severe inflammatory responses.
  • Prompt drug withdrawal is essential for successful management and recovery.