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Related Concept Videos

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:...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
[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.
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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...

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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rac-3,9-Bis(3-chloro-phen-yl)-2,4,8,10-tetra-oxaspiro-[5.5]undeca-ne.

Zhengyi Li1, Beibei Zhou, Liang Chen

  • 1Key Laboratory of Fine Chemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|November 8, 2011
PubMed
Summary

This study details the crystal structure of a dichloro-organic compound, revealing chair conformations in its heterocyclic rings and a specific dihedral angle between benzene rings. Molecules form a racemic crystal linked by weak intermolecular interactions.

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Spirocyclic compounds, featuring two rings sharing a single atom, exhibit unique conformational behaviors.

Purpose of the Study:

  • To elucidate the detailed crystal structure of the title compound, C(19)H(18)Cl(2)O(4).
  • To analyze the conformational preferences of the heterocyclic rings and the spatial relationship between the benzene rings.
  • To investigate the intermolecular interactions governing the crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, dihedral angles, and intermolecular contacts.

Main Results:

  • The two six-membered heterocycles adopt chair conformations around the spiro-carbon atom.
  • A dihedral angle of 7.2(1)° was measured between the two benzene rings.
  • The crystal structure is racemic, with R and S enantiomers generated by symmetry elements of the centrosymmetric space group.
  • Weak intermolecular C-H⋯π and C-H⋯O interactions were identified, linking the molecules in the crystal lattice.

Conclusions:

  • The study provides precise structural data for the title compound, highlighting its specific conformational characteristics.
  • The identified intermolecular interactions offer insights into the factors stabilizing the racemic crystal packing.
  • This structural information can serve as a basis for further studies on related compounds and their potential applications.