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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
2-(Pyrimidin-2-yl-oxy)phenol.
Shah Bakhtiar Nasir1, Zanariah Abdullah, Zainal A Fairuz
1Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.
Summary
This study details the crystal structure of C(10)H(8)N(2)O(2), revealing a significant dihedral angle between its pyrimidine and benzene rings. Molecular interactions, including hydrogen bonds and pi-pi stacking, dictate the compound
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Crystal packing forces, such as hydrogen bonding and pi-pi interactions, play a significant role in the assembly of molecules in the solid state.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(10)H(8)N(2)O(2).
- To analyze the intermolecular interactions governing the compound's self-assembly in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of hydrogen bonding (O-H⋯N) and C-H⋯π interactions.
- Investigation of pi-pi stacking interactions between pyrimidine rings.
Main Results:
- A notable dihedral angle of 71.03(7)° was observed between the pyrimidine and benzene rings.
- Molecules form dimeric aggregates through twofold symmetry-related O-H⋯N hydrogen bonds.
- Supramolecular chains along the b-axis are formed via C-H⋯π contacts and cross-linked by pyrimidine pi-pi interactions.
Conclusions:
- The crystal structure of C(10)H(8)N(2)O(2) is characterized by a significant twist between its aromatic rings.
- Specific intermolecular forces dictate the formation of dimeric aggregates, chains, and networks in the solid state.
- The findings provide insights into the structure-property relationships of related organic compounds.
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02:23Structure and Nomenclature of Alcohols and Phenols
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.
As with other organic compounds, alcohols and phenols...
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.
As with other organic compounds, alcohols and phenols...
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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.
01:17Oxidation of Phenols to Quinones
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
02:32Physical Properties of Alcohols and Phenols
Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
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Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...
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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...
01:57Preparation of Diols and Pinacol Rearrangement
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.