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Related Concept Videos

Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
Other Nuclides: 31P, 19F, 15N NMR01:16

Other Nuclides: 31P, 19F, 15N NMR

Many organic, inorganic, and biological molecules contain spin-half nuclei such as nitrogen-15, fluorine-19, and phosphorus-31. As a result, NMR studies of these nuclei have found extensive applications in chemical and biological research.
While fluorine-19 and phosphorous-31 have high natural abundances (100%) and positive gyromagnetic ratios, nitrogen-15 has a low natural abundance and a negative gyromagnetic ratio. However, nitrogen-15 is still preferred over nitrogen-14 (which has a high...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

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 number...
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

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 double...

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Updated: May 24, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

ent-(15S)-Pimar-8(14)-ene-15,16-diol.

Hoong-Kun Fun, Suchada Chantrapromma, Charoen Pakhathirathien

    Acta Crystallographica. Section E, Structure Reports Online
    |February 21, 2012
    PubMed
    Summary
    This summary is machine-generated.

    A novel ent-pimarane diterpenoid was isolated from Ceriops tagal stem bark. Its crystal structure reveals specific ring conformations and intermolecular hydrogen bonding in the solid state.

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    Published on: October 30, 2018

    Area of Science:

    • Natural Products Chemistry
    • Organic Chemistry
    • Crystallography

    Background:

    • Ceriops tagal is a mangrove species known for its rich phytochemical constituents.
    • Diterpenoids, a class of natural products, exhibit diverse biological activities.
    • Understanding the structure of isolated compounds is crucial for further research.

    Purpose of the Study:

    • To isolate and characterize a novel ent-pimarane diterpenoid from Ceriops tagal.
    • To elucidate the crystal structure of the isolated compound.
    • To investigate the conformational preferences and intermolecular interactions in the solid state.

    Main Methods:

    • Isolation of the compound using chromatographic techniques.
    • Structure determination via spectroscopic methods (e.g., NMR, MS).
    • Single-crystal X-ray diffraction analysis for crystallographic data.

    Main Results:

    • An ent-pimarane diterpenoid, (S)-1-[(2S,4aR,8aR)-2,4b,8,8-tetra-methyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodeca-hydro-phenanthren-2-yl]ethane-1,2-diol, was successfully isolated.
    • The crystal structure revealed two conformationally similar independent molecules in the asymmetric unit.
    • Specific conformations of the fused ring system (chair for cyclohexane, envelope for cyclohexene) and O-H⋯O hydrogen bonding were observed.

    Conclusions:

    • The study successfully identified and characterized a new ent-pimarane diterpenoid from Ceriops tagal.
    • The crystallographic analysis provides detailed insights into the compound's solid-state structure and molecular packing.
    • This structural information can serve as a basis for understanding its potential biological activities.