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Conformations of Cyclohexane

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Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...

Structures of Carboxylic Acid Derivatives

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Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
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C–C Bond Formation: Aldol Condensation Overview

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Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.

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The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
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Updated: Jul 16, 2026

Identification of Fatty Acids in Bacillus cereus

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Published on: December 5, 2016

Weak, improper, C-O...H-C hydrogen bonds in the dimethyl ether dimer.

Yoshio Tatamitani¹, Bingxin Liu, Jun Shimada

¹Department of Chemistry, Faculty of Science, Shizuoka University, Ohya, Shizuoka 422-8529 Japan.

Journal of the American Chemical Society

|March 14, 2002

Summary

Dimethyl ether dimer ((DME)(2)) exhibits a C(s) geometry, stabilized by three C-H...O hydrogen bonds. This study reveals blue-shifted hydrogen bonding, a rare interaction, with implications for molecular interactions.

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Area of Science:

Physical Chemistry
Spectroscopy
Computational Chemistry

Background:

Dimethyl ether dimer ((DME)(2)) is a weakly bound complex.
Understanding non-covalent interactions is crucial in chemistry and biology.
Hydrogen bonding plays a significant role in molecular structure and interactions.

Purpose of the Study:

To investigate the structure and bonding of the dimethyl ether dimer.
To characterize the nature of the C-H...O hydrogen bonds in the dimer.
To explore the phenomenon of blue-shifted hydrogen bonding in this system.

Main Methods:

Molecular beam Fourier transform microwave spectroscopy.
Free jet millimeter wave absorption spectroscopy.
High-level ab initio calculations.
Analysis of various isotopomers of dimethyl ether dimer.

Main Results:

The ground-state rotational spectrum of (DME)(2) was assigned, revealing a C(s) geometry.
Three weak C-H...O hydrogen bonds stabilize the dimer, with an average interaction energy of 1.9 kJ/mol.
Evidence for improper, blue-shifted hydrogen bonding was found, characterized by a C-H bond shortening of 0.0014 Å.

Conclusions:

The dimethyl ether dimer is stabilized by three C-H...O hydrogen bonds.
The observed hydrogen bonding is blue-shifted, a less common type of interaction.
The findings contribute to the understanding of weak interactions and hydrogen bonding in molecular complexes.