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Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
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Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although...
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Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
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The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
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4-Formyl-2-nitro-phenyl benzoate.

Rodolfo Moreno-Fuquen1, Geraldine Hernandez1, Alan R Kennedy2

  • 1Departamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia.

Acta Crystallographica. Section E, Structure Reports Online
|April 26, 2014
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Summary
This summary is machine-generated.

This study details the crystal structure of a nitroaryl benzoate derivative. Its planar ester group and specific dihedral angles between aromatic rings influence its crystal packing into helical chains via C-H⋯O interactions.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Nitroaryl compounds and benzoate esters are important structural motifs in medicinal chemistry and materials science.
  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.

Purpose of the Study:

  • To elucidate the crystal structure of the nitroaryl benzoate derivative C14H9NO5.
  • To analyze the molecular geometry, including dihedral angles between aromatic rings and the planarity of the ester moiety.
  • To investigate the intermolecular interactions and crystal packing.

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 was performed.
  • Identification of intermolecular interactions, such as C-H⋯O hydrogen bonds, was conducted.

Main Results:

  • The crystal structure of C14H9NO5 was successfully determined.
  • A significant dihedral angle of 46.37(8)° was observed between the two aromatic rings.
  • The central ester group was found to be nearly planar, with specific dihedral angles relative to the substituted phenyl and benzoate rings.
  • Weak C-H⋯O interactions were identified as the driving force for the formation of helical chains along the [100] direction in the crystal.

Conclusions:

  • The study provides a detailed understanding of the molecular conformation and crystal packing of the nitroaryl benzoate derivative.
  • The observed planarity of the ester group and the specific dihedral angles are key features of this molecule's solid-state structure.
  • The helical chain formation mediated by C-H⋯O interactions highlights the importance of weak intermolecular forces in supramolecular assembly.