Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

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...

Chair Conformation of Cyclohexane

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...

Stereoisomerism of Cyclic Compounds

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 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...

Newman Projections

Newman Projections

Different notations are used to represent the three-dimensional structure of molecules on two-dimensional surfaces. One of the most commonly used representations is the dash-wedge formula. The dashed wedges, solid wedges, and the plane lines indicate the groups situated behind the plane, coming out of the plane, and in the plane, respectively.
The organic molecules rotate across the single bonds leading to numerous temporary three-dimensional structures of varying energy known as...

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.

You might also read

Related Articles

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

Sort by

Same author

Photochemical C4-Selective C-H Amination of Quinolines via <i>N</i>-Shift of Heteroaryl Azides.

Organic letters·2026

Same author

Stereodefined Synthesis of 3-Difluoromethyl-Benzoxaboroles: Novel Antimicrobials with Unlocked H-Bonding.

Organic letters·2026

Same author

Sustainable electrochemical synthesis of a new isoxazoline scaffold as turn inducer to build parallel β-hairpins.

Organic & biomolecular chemistry·2026

Same author

Cannabizetol, a Novel Cannabinoid: Chemical Synthesis, Anti-inflammatory Activity and Extraction from <i>Cannabis sativa</i> L.

Journal of natural products·2025

Same author

Asymmetric Total Synthesis of (-)-Glycybridin B, a Pharmacophore Screened Candidate for Tubulin Binding.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025

Same author

Structure-Based Discovery of Hsp90/HDAC6 Dual Inhibitors Targeting Aggressive Prostate Cancer.

Journal of medicinal chemistry·2025

Same journal

Organophosphine-Promoted Decarbynylative Hydrocarbenylation of the Carbon-Carbon Triple Bond.

Organic letters·2026

Same journal

Total Syntheses of BE-54238A and -B.

Organic letters·2026

Same journal

Visible Light-Induced <i>N</i>-Phenylbenzo[<i>c</i>]phenothiazine-Catalyzed α-C(sp<sup>3</sup>)-H Phosphonylation of Secondary Amines via Intramolecular 1,5-HAT.

Organic letters·2026

Same journal

Cobalt-Stabilized Propargylic Oxocarbenium Ions Enable Direct and Asymmetric Nickel(II) Catalyzed Aldol-Like Reactions.

Organic letters·2026

Same journal

Photoinduced Regioselective Sulfonylation/Cyclization of <i>N</i>-Cinnamylenamides toward Sulfonylated Tetrahydropyridines via Catalytic Electron Donor-Acceptor Complexes.

Organic letters·2026

Same journal

Amine-Enabled Electron Donor-Acceptor Complex Catalysis for Cyclopropanation.

Organic letters·2026

See all related articles

Search research articles

Related Experiment Video

Updated: Sep 10, 2025

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy

Published on: September 17, 2017

Rotational Motion in Bispidines: A Conformational Study.

Francesco Migliano¹, Luca Pozzi¹, Andrea Citarella¹

¹Department of Chemistry, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy.

Organic Letters

|August 26, 2025

Summary

This summary is machine-generated.

N-substituted bispidines exhibit restricted rotation due to substituent effects. Computational and experimental methods reveal factors controlling this motion and identify resulting rotamers.

More Related Videos

15N CPMG Relaxation Dispersion for the Investigation of Protein Conformational Dynamics on the µs-ms Timescale

15N CPMG Relaxation Dispersion for the Investigation of Protein Conformational Dynamics on the µs-ms Timescale

Published on: April 19, 2021

Author Spotlight: Exploring Intrinsically Disordered Protein Dynamics Through NMR Relaxation Experiments

Author Spotlight: Exploring Intrinsically Disordered Protein Dynamics Through NMR Relaxation Experiments

Published on: November 1, 2024

Related Experiment Videos

Last Updated: Sep 10, 2025

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy

Published on: September 17, 2017

15N CPMG Relaxation Dispersion for the Investigation of Protein Conformational Dynamics on the µs-ms Timescale

15N CPMG Relaxation Dispersion for the Investigation of Protein Conformational Dynamics on the µs-ms Timescale

Published on: April 19, 2021

Author Spotlight: Exploring Intrinsically Disordered Protein Dynamics Through NMR Relaxation Experiments

Author Spotlight: Exploring Intrinsically Disordered Protein Dynamics Through NMR Relaxation Experiments

Published on: November 1, 2024

Area of Science:

Organic Chemistry
Molecular Conformation
Computational Chemistry

Background:

Bispidines are bicyclic amines with unique structural properties.
Restricted rotation in organic molecules can influence their reactivity and function.
Understanding conformational preferences is crucial for molecular design.

Purpose of the Study:

To investigate the conformational analysis of N-substituted bispidines.
To identify factors governing restricted rotational motion.
To characterize the rotamers resulting from substituent-induced rotation.

Main Methods:

Computational studies of transition states for rotation.
Experimental characterization of rotamers.
Conformational analysis using spectroscopy and modeling.

Main Results:

Specific N-substituents were found to induce significant rotational barriers.
Computational models accurately predicted the observed rotamer populations.
The interplay between steric and electronic effects dictates rotational restriction.

Conclusions:

The study elucidates the conformational behavior of N-substituted bispidines.
Restricted rotation is a tunable property influenced by substituent choice.
Findings provide insights for designing molecules with specific conformational constraints.