Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Conformations of Ethane and Propane02:18

Conformations of Ethane and Propane

19.7K
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...
19.7K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

16.9K
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...
16.9K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

17.5K
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...
17.5K
Conformations of Butane02:20

Conformations of Butane

20.9K
Unlike ethane and propane that have only two major conformations, butane has more than two conformers. The staggered form of butane in which the bulky methyl groups on the two carbons are placed on opposite sides, that is, at a dihedral angle of 180°, is the lowest energy, most stable form — called the anti conformer. This conformation is stabilized due to the absence of steric repulsion between the largely spaced out methyl groups. The other two staggered conformations are...
20.9K
Solvating Effects02:12

Solvating Effects

9.3K
An understanding of the solvating effect helps rationalize the relation between solvation and acidity of the compound. In addition, this also explains the relative stability of conjugate bases for compounds with different pKa values. This lesson details, in-depth, the principle of solvating effects. The strength of an acid and the stability of its corresponding conjugate base are determined using pKa values. This observed relationship is a consequence of solvation, which is the interaction...
9.3K
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

1.4K
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...
1.4K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

HyDRA-II: spectroscopic results and BEsT guesses for the mono- and dihydrate blind challenge.

Physical chemistry chemical physics : PCCP·2026
Same author

Enantioselective synthesis of configurationally stable [5]helicenes containing 1,2-azaborine units.

Chemical science·2026
Same author

Isocyanides Versus Nitriles: Divergent Hydrogen Bonding Behavior Driven by the Balance Between Dispersive and Electrostatic Forces.

Chemphyschem : a European journal of chemical physics and physical chemistry·2026
Same author

Synthesis and reactivity of a strongly pyramidalized P(III)-compound embedded into a pyrrolide (ONO)<sup>3-</sup> pincer ligand.

Chemical communications (Cambridge, England)·2026
Same author

Probing Hydrogen Activation in a Dimetal Dihydride Complex by Symmetric Exchange with Parahydrogen.

Journal of the American Chemical Society·2026
Same author

A Diazo-free Equivalent of the Unsubstituted Carbyne Cation: Straightforward Synthesis of Naphthalenes and Pyridines via [<sup>12/13</sup>CH]<sup>+</sup> Insertion.

Journal of the American Chemical Society·2026

Related Experiment Video

Updated: Apr 16, 2026

Spatial Separation of Molecular Conformers and Clusters
10:37

Spatial Separation of Molecular Conformers and Clusters

Published on: January 9, 2014

11.9K

Bracketing subtle conformational energy differences between self-solvated and stretched trifluoropropanol.

Matthias Heger1, Katharina E Otto, Ricardo A Mata

  • 1Institut für Physikalische Chemie, Universität Göttingen, Tammannstr. 6, 37077 Göttingen, Germany. msuhm@gwdg.de.

Physical Chemistry Chemical Physics : PCCP
|March 18, 2015
PubMed
Summary

The intramolecular hydrogen bond in 3,3,3-trifluoropropanol (TFP) stabilizes its structure, creating two main forms. This study quantizes the energy difference between these TFP conformers using spectroscopy and calculations.

More Related Videos

Covalent Attachment of Single Molecules for AFM-based Force Spectroscopy
10:37

Covalent Attachment of Single Molecules for AFM-based Force Spectroscopy

Published on: March 16, 2020

10.5K
Optical Tweezers to Study RNA-Protein Interactions in Translation Regulation
12:26

Optical Tweezers to Study RNA-Protein Interactions in Translation Regulation

Published on: February 12, 2022

6.1K

Related Experiment Videos

Last Updated: Apr 16, 2026

Spatial Separation of Molecular Conformers and Clusters
10:37

Spatial Separation of Molecular Conformers and Clusters

Published on: January 9, 2014

11.9K
Covalent Attachment of Single Molecules for AFM-based Force Spectroscopy
10:37

Covalent Attachment of Single Molecules for AFM-based Force Spectroscopy

Published on: March 16, 2020

10.5K
Optical Tweezers to Study RNA-Protein Interactions in Translation Regulation
12:26

Optical Tweezers to Study RNA-Protein Interactions in Translation Regulation

Published on: February 12, 2022

6.1K

Area of Science:

  • Physical Chemistry
  • Molecular Spectroscopy
  • Computational Chemistry

Background:

  • Intramolecular hydrogen bonds significantly influence molecular conformation and stability.
  • Fluorinated alcohols present unique conformational landscapes due to fluorine's electronegativity.
  • Understanding conformer energy differences is crucial for predicting molecular behavior.

Purpose of the Study:

  • To investigate the conformational landscape of 3,3,3-trifluoropropanol (TFP).
  • To quantify the energy difference between the two most stable TFP conformers.
  • To elucidate the role of the intramolecular OH···F hydrogen bond in TFP's structure.

Main Methods:

  • Raman spectroscopy in supersonic expansions.
  • High-level quantum-chemical calculations.
  • Analysis of torsional potential energy surfaces.

Main Results:

  • The intramolecular OH···F hydrogen bond in TFP reorders conformers and increases the energy gap between the two most stable structures.
  • The energy difference between the two most stable TFP conformers was determined to be 1.7(5) kJ mol(-1).
  • Conformer interconversion is driven by consecutive backbone and OH torsional motions.

Conclusions:

  • TFP exists as a bistable cold molecule with distinct trans or gauche backbone conformations.
  • The OH group's interaction is key to modulating the energy difference and the barrier between heavy atom frames.
  • Supersonic jet cooling provides a unique environment to study molecular conformers and their interconversion pathways.