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Related Concept Videos

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)01:20

¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)

When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
Directing Effect of Substituents: meta-Directing Groups01:09

Directing Effect of Substituents: meta-Directing Groups

Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are called meta directors. All meta directors either have a positive charge on the atom directly bonded to the ring or a partial positive charge. These groups function by withdrawing electrons from the ring through inductive and resonance effects. Consider the carbocation intermediates formed upon the addition of an electrophile on nitrobenzene at the ortho, meta, and para...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Published on: August 16, 2018

Dimethyl 3-phenyl-penta-nedioate.

Peng Zhang1, Feng Fu, Ni Wang

  • 1Department of Chemistry and Chemical Engineering, Shaanxi Key Laboratory of Chemical Reaction Engineering, Yan'an University, Shaanxi 716000, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 19, 2011
PubMed
Summary
This summary is machine-generated.

The crystal structure of C(13)H(16)O(4) reveals twisted carboxylate groups with a dihedral angle of 23.80 degrees. Molecules form chains via weak C-H⋯O hydrogen bonds in this organic compound.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding molecular arrangements is key in crystal engineering.
  • Carboxylate groups influence crystal packing and intermolecular interactions.
  • Hydrogen bonding plays a crucial role in forming supramolecular structures.

Purpose of the Study:

  • To determine the crystal structure of the title compound, C(13)H(16)O(4).
  • To analyze the conformation of terminal carboxylate groups.
  • To investigate the intermolecular interactions and resulting supramolecular architecture.

Main Methods:

  • Single-crystal X-ray diffraction was employed to elucidate the molecular structure.
  • Analysis of bond lengths, bond angles, and dihedral angles.
  • Identification and analysis of intermolecular interactions, specifically C-H⋯O hydrogen bonds.

Main Results:

  • The crystal structure of C(13)H(16)O(4) was successfully determined.
  • A significant dihedral angle of 23.80(9)° was observed between the terminal carboxylate groups.
  • Weak intermolecular C-H⋯O hydrogen bonds were identified, leading to the formation of supramolecular chains along the a axis.

Conclusions:

  • The title compound exhibits a specific molecular conformation with twisted carboxylate groups.
  • Intermolecular C-H⋯O hydrogen bonds are the primary driving force for the observed supramolecular chain formation.
  • The findings contribute to the understanding of crystal packing and hydrogen bonding in organic molecules.