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Related Concept Videos

Stereoisomers02:32

Stereoisomers

On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to restricted...
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Stereoisomerism02:52

Stereoisomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
Naming Enantiomers02:21

Naming Enantiomers

The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three steps:...

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Updated: May 21, 2026

A Strategy for Sensitive, Large Scale Quantitative Metabolomics
14:18

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Published on: May 27, 2014

3-O-Methyl-1-isomangostin.

Nawong Boonnak, Suchada Chantrapromma, Hoong-Kun Fun

    Acta Crystallographica. Section E, Structure Reports Online
    |June 22, 2012
    PubMed
    Summary

    This study details the crystal structure of a novel xanthone derivative, revealing its planar xanthone core and specific ring conformations. Molecular interactions and hydrogen bonding influence its crystal packing.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure

    Background:

    • Xanthone derivatives are a class of organic compounds with diverse biological activities.
    • Understanding the precise three-dimensional structure of these molecules is crucial for structure-activity relationship studies.

    Purpose of the Study:

    • To elucidate the crystal structure of a specific xanthone derivative.
    • To analyze the molecular conformation and intermolecular interactions in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed.
    • The crystal structure was solved and refined to determine atomic coordinates and bond parameters.

    Main Results:

    • The xanthone ring system exhibits a nearly planar geometry (r.m.s. deviation of 0.1038 Å).

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  • The chromane ring adopts a half-chair conformation, and the prenyl substituent is in an axial, (+)-anti-clinal conformation.
  • Intramolecular C-H⋯O interactions form S(6) ring motifs, and intermolecular O-H⋯O and C-H⋯O hydrogen bonds link molecules into ribbons.
  • A π-π stacking interaction was observed between xanthone rings with a centroid-centroid distance of 3.5413 Å.

    • Conclusions:

    • The study provides detailed structural insights into a novel xanthone derivative.
    • The observed intermolecular interactions and π-π stacking are key features of its crystal packing.
    • This structural information can aid in the design of new xanthone-based compounds with tailored properties.