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Related Concept Videos

Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

5.5K
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the...
5.5K
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

3.4K
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
3.4K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

13.3K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
13.3K
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

8.6K
Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the...
8.6K
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

17.0K
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...
17.0K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.3K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.3K

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Related Experiment Video

Updated: Apr 30, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Energetic and structural study of bisphenols.

Juan Z Dávalos1, Rebeca Herrero, José C S Costa

  • 1Instituto de Quı́mica-Fı́sica "Rocasolano", CSIC , Serrano 119, 28006 Madrid, Spain.

The Journal of Physical Chemistry. A
|May 3, 2014
PubMed
Summary

This study determined thermochemical properties of bisphenols A, E, F, and AP. Energetic substituent effects were found to be transferable from diphenylalkanes to bisphenols, confirming experimental data.

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Area of Science:

  • Physical Chemistry
  • Computational Chemistry
  • Organic Chemistry

Background:

  • Bisphenols are widely used in polymer production.
  • Understanding their thermochemical properties is crucial for material science applications.
  • Previous studies have focused on specific bisphenol derivatives, necessitating a comparative analysis.

Purpose of the Study:

  • To experimentally determine standard enthalpies of sublimation and formation for bisphenols A, E, F, and AP.
  • To computationally investigate structural effects using M05-2X density functional theory.
  • To validate experimental findings through theoretical calculations and explore substituent effect transferability.

Main Methods:

  • Experimental determination of standard enthalpies of sublimation and formation at 298.15 K.
  • Computational analysis using M05-2X density functional theory.
  • Isodesmic reaction scheme for theoretical validation.

Main Results:

  • Experimentally determined thermochemical data for bisphenols A, E, F, and AP.
  • Computational study elucidated structural influences on properties.
  • High consistency between experimental and theoretical results was achieved.
  • Energetic substituent effects were confirmed as transferable.

Conclusions:

  • The study provides a comprehensive dataset of thermochemical properties for key bisphenols.
  • Theoretical calculations support and validate the experimental findings.
  • The transferability of energetic substituent effects offers a valuable predictive tool for related compounds.