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Related Concept Videos

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

1.2K
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...
1.2K
Structure of Amines01:19

Structure of Amines

3.2K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are...
3.2K
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

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

1.7K
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.
1.7K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.5K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
3.5K
IR Spectrum Peak Splitting: Symmetric vs Asymmetric Vibrations01:08

IR Spectrum Peak Splitting: Symmetric vs Asymmetric Vibrations

1.7K
Identical bonds within a polyatomic group can stretch symmetrically (in-phase) or asymmetrically (out-of-phase). Similar to hydrogen bonding, these vibrations also influence the shape of the IR peak. Generally, asymmetric stretching frequencies are higher than symmetric stretching frequencies. For example, primary amines exhibit two distinct IR peaks between 3300–3500 cm−1 corresponding to the symmetric and asymmetric N-H stretching, while secondary amines exhibit a single...
1.7K
NMR Spectroscopy Of Amines01:19

NMR Spectroscopy Of Amines

10.8K
In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range between δ 0.5 and 5 ppm. The exact position in this range depends on several factors, including sample concentration, hydrogen bonding, and the type of solvent used. Since amine protons undergo fast proton exchange in solution, the protons are labile and therefore do not participate in any splitting with adjacent protons. Thus, the observed peak is...
10.8K

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Updated: Jan 12, 2026

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy
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Aromatic Amide Foldamers Show Conformation-Dependent Electronic Properties.

Rajarshi Samajdar1,2, Xiaolin Liu3, Kazusa Kuyama4

  • 1Department of Chemical and Biomolecular Engineering, University of Illinois at Urbana-Champaign, Urbana, 61801, Illinois.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|November 8, 2025
PubMed
Summary
This summary is machine-generated.

Molecular shape significantly impacts electron transport. Folded amide molecules show lower conductance than extended ones due to different transport mechanisms, highlighting the importance of three-dimensional (3D) conformations.

Keywords:
electron transportelectron tunnelingfoldamersmolecular electronicssupramolecular chemistry

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Area of Science:

  • Organic electronics
  • Molecular biophysics
  • Supramolecular chemistry

Background:

  • Electron transport in organic and biomolecules depends on electronic structure and conformation.
  • Understanding the influence of intramolecular interactions and 3D conformations on electron transport remains a challenge.

Purpose of the Study:

  • To characterize the electronic properties of aromatic amide foldamers with distinct 3D structures.
  • To investigate the relationship between molecular conformation and electron transport behavior.

Main Methods:

  • Single-molecule electronic experiments
  • Bulk spectroscopic characterization
  • Density functional theory (DFT) calculations

Main Results:

  • Extended secondary amides (trans-conformation) showed a fourfold increase in molecular conductance compared to folded N-methylated tertiary amides (cis-conformation).
  • Extended amides utilize a through-bond electron transport mechanism, while folded amides rely on through-space transport.
  • Extended amides exhibit a smaller HOMO-LUMO gap and higher transmission values than folded amides.

Conclusions:

  • 3D molecular conformations play a critical role in determining the electronic properties of single-molecule junctions.
  • Tailoring molecular structure offers a pathway to control electron transport in organic electronic devices.