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Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Structure and Nomenclature of Alcohols and Phenols02:23

Structure 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...
Physical Properties of Ethers02:17

Physical Properties of Ethers

Overview
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols. Ethers are considered...
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.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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1,2-Bis(4-meth-oxy-phen-oxy)ethane.

Jun Ji1, Xiuqin Zhang, Kai Wang

  • 1School of Petrochemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 2, 2013
PubMed
Summary
This summary is machine-generated.

This study details the molecular structure of C16H18O4, revealing its twofold rotational symmetry and crystal network formed by C-H⋯O hydrogen bonds. The findings offer insights into molecular arrangement and intermolecular interactions.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure Analysis

Background:

  • Understanding the precise three-dimensional arrangement of atoms within organic molecules is crucial for predicting their chemical and physical properties.
  • Symmetry elements play a significant role in defining molecular geometry and influencing crystal packing.

Purpose of the Study:

  • To elucidate the complete molecular structure of the title compound, C16H18O4.
  • To analyze the symmetry elements and key conformational parameters of the molecule.
  • To investigate the intermolecular interactions and crystal packing in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and torsion angles provided detailed conformational information.
  • Identification of hydrogen bonding interactions and assessment of crystal network formation.

Main Results:

  • The molecule of C16H18O4 possesses a twofold rotational symmetry axis bisecting the central C-C bond.
  • The O-C-C-O torsion angle was determined to be 69.45(16)°.
  • Symmetrically related benzene rings are inclined at an angle of 64.91(8)°.
  • The crystal structure is characterized by a three-dimensional network formed through C-H⋯O hydrogen bonds.

Conclusions:

  • The structural analysis confirms the specific molecular geometry and symmetry of C16H18O4.
  • The identified hydrogen bonding network dictates the extended crystal structure.
  • These findings contribute to the understanding of structure-property relationships in organic crystalline materials.