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Conformations of Cycloalkanes

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3 hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...

Conformations of Cyclohexane

Conformations of Cyclohexane

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.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...

Fischer Projections

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Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines. While...

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.

Structures of Carboxylic Acid Derivatives

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Structure of Carboxylic Acid Derivatives
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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Conformational Map of Phenolic Acids.

Vanessa Cortijo¹, Elena R Alonso¹, Santiago Mata¹

¹Grupo de Espectroscopia Molecular (GEM), Edificio Quifima, Laboratorios de Espectroscopia y Bioespectroscopia, Parque Cientı́fico UVa, Unidad Asociada CSIC, Universidad de Valladolid , 47011, Valladolid, Spain .

The Journal of Physical Chemistry. A

|December 8, 2017

Summary

Researchers mapped the molecular shapes of trans-cinnamic and p-coumaric acids using laser ablation and chirped pulse Fourier transform microwave spectroscopy (CP-FTMW). This technique identified multiple conformers for each acid, aiding in their unambiguous identification.

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Area of Science:

Molecular spectroscopy
Physical chemistry
Organic chemistry

Background:

Phenolic acids are important organic compounds.
Understanding their molecular structure is key to their function.
Previous methods lacked the resolution to map complex structures.

Purpose of the Study:

To create the first conformational map of trans-cinnamic and p-coumaric acids.
To characterize the different spatial arrangements (conformers) of these molecules.
To demonstrate the power of CP-FTMW spectroscopy for molecular identification.

Main Methods:

Laser ablation for sample vaporization.
Chirped pulse Fourier transform microwave (CP-FTMW) spectroscopy for high-resolution analysis.
Supersonic expansion to isolate molecules and simplify spectra.
Analysis of rotational spectra to determine spectroscopic constants.

Main Results:

Successfully mapped the conformational landscape of trans-cinnamic and p-coumaric acids.
Identified two distinct conformers for trans-cinnamic acid.
Characterized four distinct conformers for trans-p-coumaric acid.
Spectroscopic constants obtained matched theoretical predictions for unambiguous identification.

Conclusions:

CP-FTMW spectroscopy is a powerful tool for characterizing molecular conformers.
The conformational maps provide a basis for understanding the properties and reactivity of these phenolic acids.
This study sets a precedent for conformational analysis of similar organic molecules.