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Related Concept Videos

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...
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

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...
Directing Effect of Substituents: ortho–para-Directing Groups01:14

Directing Effect of Substituents: ortho–para-Directing Groups

Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered ortho–para directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate electrons...
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
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...
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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2,2'-Bis(4-nitro-phen-oxy)-1,1'-binaphth-yl.

Wen-Xian Liang1, Zhi-Rong Qu

  • 1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary

Researchers synthesized a novel compound, C(32)H(20)N(2)O(6), using 1,1'-binaphthyl-2,2'-diol and 4-nitro-phenol. The resulting crystal structure features a significant dihedral angle and hydrogen-bonded chains.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Published on: June 20, 2014

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Materials Science

Background:

  • 1,1'-binaphthyl-2,2'-diol is a chiral building block with applications in asymmetric synthesis.
  • Nitro-phenols are versatile intermediates in the synthesis of dyes, pharmaceuticals, and energetic materials.

Purpose of the Study:

  • To synthesize and characterize a novel compound derived from 1,1'-binaphthyl-2,2'-diol and 4-nitro-phenol.
  • To investigate the structural properties, including dihedral angles and crystal packing, of the synthesized compound.

Main Methods:

  • Synthesis via nucleophilic substitution reaction between 1,1'-binaphthyl-2,2'-diol and 4-nitro-phenol.
  • Characterization using X-ray crystallography to determine molecular structure and crystal packing.

Main Results:

  • Successful synthesis of the title compound with molecular formula C(32)H(20)N(2)O(6).
  • X-ray diffraction analysis revealed a dihedral angle of 73.70(5)° between the two naphthalene systems.
  • Crystal structure exhibits intermolecular C-H⋯O hydrogen bonds, forming chains along the c-axis.

Conclusions:

  • The study reports the successful synthesis and structural elucidation of a novel binaphthyl derivative.
  • The observed dihedral angle and hydrogen bonding patterns provide insights into the molecule's solid-state behavior.
  • This compound may serve as a basis for developing new functional materials.