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Related Concept Videos

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...
[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.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...

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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

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Cyclotridecanone 2,4-dinitrophenylhydrazone.

Edward J Valente1, Diwaker M Pawar, Frank R Fronczek

  • 1Department of Chemistry and Biochemistry, Mississippi College, Clinton, MS 39058, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|August 7, 2008
PubMed
Summary
This summary is machine-generated.

The study reveals the preferred [337] conformation of cyclotridecanone 2,4-dinitrophenylhydrazone. This conformation, with its unique ring structure and hydrogen bonding, provides insights into the preferred shapes of medium-sized rings.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Conformation

Background:

  • Understanding the conformational preferences of medium-sized rings (10-14 members) is crucial in organic chemistry.
  • Cyclic compounds exhibit diverse spatial arrangements, influencing their reactivity and physical properties.

Purpose of the Study:

  • To determine the specific three-dimensional structure of cyclotridecanone 2,4-dinitrophenylhydrazone.
  • To elucidate the preferred conformation of the 13-membered carbocyclic ring and associated functional groups.

Main Methods:

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

Main Results:

  • The 13-membered carbocycle adopts a triangular [337] conformation.
  • The 2,4-dinitrophenylhydrazone group is positioned nearly perpendicular to the ring (dihedral angle of 82.66°).
  • Intramolecular hydrogen bonding and weaker C-H...O interactions were identified.

Conclusions:

  • The [337] conformation is indicated as the preferred structure for cyclotridecane and similar 13-membered rings.
  • The observed crystal packing and intermolecular interactions support the conformational findings.