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NMR Spectroscopy of Benzene Derivatives

NMR Spectroscopy of Benzene Derivatives

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 constants depend...

Hydrolysis of Chlorobenzene to Phenol: Dow Process

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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 eliminated to generate the benzyne...

Nomenclature of Aromatic Compounds with Multiple Substituents

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

Chemotherapy-Induced Nausea and Vomiting: Dopamine Receptor Antagonists

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Dopamine receptor antagonists, also known as antipsychotic agents, are critical in managing chemotherapy-induced vomiting. These antiemetic agents block dopamine receptors in the chemoreceptor trigger zone (CTZ), inhibiting signal transmission to the vomiting center. Antipsychotic agents encompass phenothiazines (PTZ), butyrophenones, benzamides, and thienobenzodiazepines (Zyprexa), which are utilized for their antiemetic and sedative properties.
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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Nucleophilic Aromatic Substitution: Elimination–Addition

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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Related Experiment Video

Updated: May 30, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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2,6-Dichloro-N-phenyl-benzamide.

Hui Liu, Ning Xu, Bo Yang

Acta Crystallographica. Section E, Structure Reports Online

|August 13, 2011

Summary

This study reveals distinct molecular arrangements in a novel organic compound, C(13)H(9)Cl(2)NO. Molecules form hydrogen-bonded chains in the crystal structure, influencing their spatial orientation.

Area of Science:

Crystallography
Organic Chemistry
Materials Science

Background:

Understanding molecular structure and intermolecular interactions is crucial in chemistry.
Crystal engineering aims to control solid-state properties through molecular design.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(13)H(9)Cl(2)NO.
To analyze the dihedral angles between aromatic rings and identify intermolecular interactions.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of bond lengths, bond angles, and intermolecular forces (hydrogen bonding).

Main Results:

Two independent molecules were identified in the asymmetric unit.

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Significantly different dihedral angles (48.5(3)° and 65.1(3)°) were observed between the phenyl and dichlorophenyl rings.

Intermolecular N-H⋯O hydrogen bonds link molecules into chains parallel to the c axis.

Conclusions:

The crystal structure of C(13)H(9)Cl(2)NO exhibits unique conformational diversity due to differing dihedral angles.
Hydrogen bonding plays a key role in organizing the molecules within the crystal lattice, forming 1D chains.