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Related Concept Videos

Conformations of Ethane and Propane02:18

Conformations of Ethane and Propane

In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered ethane, the...
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

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...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
Conformations of Cyclohexane02:11

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 tetrahedral value,...
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...

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Using a Cyclic Ion Mobility Spectrometer for Tandem Ion Mobility Experiments
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Published on: January 20, 2022

Specific rotation as a property to validate monosaccharide conformations.

Renato R Andrade1, Clarissa O da Silva

  • 1Departamento de Química, Universidade Federal Rural do Rio de Janeiro, km 47-Seropédica, Rio de Janeiro, Brazil.

Carbohydrate Research
|January 28, 2012
PubMed
Summary

Specific rotation values for xylopyranose conformations were calculated. Even minor structural differences significantly alter specific rotation, suggesting its use for validating theoretical monosaccharide structures.

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Area of Science:

  • Carbohydrate Chemistry
  • Computational Chemistry
  • Structural Biology

Background:

  • Understanding the conformational landscape of monosaccharides like xylopyranose is crucial.
  • Accurate prediction of their properties requires robust theoretical methods.

Purpose of the Study:

  • To calculate specific rotation ([α](D)) values for stable xylopyranose conformations.
  • To evaluate the impact of theoretical methods and solvent on geometry and [α](D).

Main Methods:

  • Quantum chemical calculations were employed to determine the 15 most stable xylopyranose conformations.
  • Specific rotation ([α](D)) values were computed for these conformers in both gas and aqueous phases.
  • The influence of different theoretical models and solvent effects on molecular geometry and [α](D) was assessed.

Main Results:

  • Calculated [α](D] values showed significant differences between distinct xylopyranose conformers.
  • The observed differences in [α](D] were larger between different conformers than across different theoretical descriptions for the same conformer.
  • Even subtle conformational changes, such as the orientation of a single hydroxyl group, led to prominent variations in [α](D] values.

Conclusions:

  • Specific rotation ([α](D)) values exhibit high sensitivity to the conformational state of xylopyranose.
  • The findings suggest that experimental [α](D) measurements can serve as a valuable tool for validating theoretically predicted monosaccharide conformations.
  • This approach aids in refining computational models for carbohydrate structures.