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Related Concept Videos

NMR Spectroscopy of Aromatic Compounds01:14

NMR Spectroscopy of Aromatic Compounds

6.5K
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.
6.5K
Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

14.8K
In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
14.8K
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

10.8K
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...
10.8K
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

10.6K
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).
10.6K
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

11.5K
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...
11.5K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

13.9K
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 +...
13.9K

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Related Experiment Video

Updated: Feb 20, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Estimating the Physicochemical Properties of Polysubstituted Aromatic Compounds Using UPPER.

Doaa Alantary1, Samuel H Yalkowsky1

  • 1College of Pharmacy, University of Arizona, 1703 E. Mabel St., Tucson, Arizona 85721.

Journal of Pharmaceutical Sciences
|October 28, 2017
PubMed
Summary
This summary is machine-generated.

The Unified Physicochemical Property Estimation Relationships (UPPER) model now predicts properties for diverse aromatic compounds. This validated approach uses only 2D structures for accurate physicochemical property estimation.

Keywords:
QSPRdrug-like propertieslog pmolecular modelingphysicochemical propertiesstructure-property relationship (SPR)thermodynamics

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Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
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Area of Science:

  • Computational chemistry
  • Physical chemistry
  • Chemical engineering

Background:

  • The Unified Physicochemical Property Estimation Relationships (UPPER) model, developed over 25 years ago, accurately predicts 9 essential physicochemical properties for hydrocarbons.
  • The model relies on additive and nonadditive descriptors and thermodynamic relationships, using only a 2D chemical structure as input.
  • Previous validation by the Yalkowsky group covered approximately 2000 aliphatic, aromatic, and polyhalogenated hydrocarbons.

Purpose of the Study:

  • To extend the applicability of the UPPER model to a broader range of compounds.
  • To include hydrogen bonding and non-hydrogen bonding aromatic compounds with various functional groups.
  • To assess the model's performance in predicting physicochemical properties for this expanded dataset.

Main Methods:

  • The study utilized the existing UPPER model framework.
  • The model was applied to a new dataset of nearly 3000 aromatic compounds with functional groups like alcohols, amines, carboxylic acids, and nitro compounds.
  • Physicochemical properties were calculated without a training set, except for enthalpies and entropies of melting and boiling.

Main Results:

  • The UPPER model demonstrated reasonable estimation capabilities for all considered physicochemical properties across the expanded compound set.
  • The model successfully predicted properties for diverse aromatic compounds, including those with hydrogen-bonding capabilities and various functional groups.
  • No training set was required for most property calculations, highlighting the model's predictive power.

Conclusions:

  • The extended UPPER model provides a valuable tool for estimating physicochemical properties of a wide array of aromatic compounds.
  • The model's reliance on 2D structures and minimal training data makes it efficient for property prediction in chemical research and development.
  • Further validation and application of the UPPER model are recommended for diverse chemical applications.