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Related Concept Videos

Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that was based on the...
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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Cycloalkanes02:28

Cycloalkanes

Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
[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.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

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Spiro-[cyclo-propane-1,3'-indolin]-2'-one.

Maosen Yuan1, Qi Wang, Yuejun Zhang

  • 1College of Science, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|November 9, 2011
PubMed
Summary
This summary is machine-generated.

This study details the molecular structure of C(10)H(9)NO, revealing a near-90-degree angle between its cyclopropane and indole rings. Molecules form chains via hydrogen bonds in the crystal structure.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • The indole scaffold is a common motif in pharmaceuticals and natural products, making its derivatives of significant scientific interest.

Purpose of the Study:

  • To elucidate the crystal structure and molecular geometry of a specific C(10)H(9)NO compound.
  • To investigate the intermolecular interactions present in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided detailed geometric information.

Main Results:

  • The dihedral angle between the cyclopropane ring and the indole ring system was determined to be 87.65(17)°.
  • Intermolecular N-H⋯O hydrogen bonds were identified, leading to the formation of one-dimensional chains along the [100] direction.

Conclusions:

  • The study provides precise structural data for the C(10)H(9)NO molecule, highlighting its non-planar conformation.
  • The observed hydrogen bonding pattern dictates the supramolecular assembly in the solid state, offering insights into crystal engineering.