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Related Concept Videos

Hydrogen Bonds00:26

Hydrogen Bonds

128.0K
Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
128.0K
Hydrogen Bonds01:04

Hydrogen Bonds

11.4K
A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
11.4K
SN2 Reaction: Transition State02:26

SN2 Reaction: Transition State

10.8K
An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
10.8K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.9K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
12.9K
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

3.8K
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
3.8K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.2K
The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...
2.2K

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Updated: Nov 2, 2025

Analyzing Protein Dynamics Using Hydrogen Exchange Mass Spectrometry
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Analyzing Protein Dynamics Using Hydrogen Exchange Mass Spectrometry

Published on: November 29, 2013

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Large transition state stabilization from a weak hydrogen bond.

Erik C Vik1, Ping Li1, Josef M Maier1

  • 1Department of Chemistry and Biochemistry, University of South Carolina Columbia SC 29208 USA shimizu@mail.chem.sc.edu.

Chemical Science
|June 14, 2021
PubMed
Summary
This summary is machine-generated.

A novel molecular rotor design revealed that intramolecular hydrogen bonds can significantly lower rotational energy barriers. This transition state stabilization exceeds intrinsic bond strength, offering insights for catalyst and enzyme mechanism design.

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Area of Science:

  • Organic Chemistry
  • Physical Chemistry
  • Computational Chemistry

Background:

  • Molecular rotors are used to study reaction dynamics.
  • Intramolecular hydrogen bonds can influence molecular conformation and reactivity.
  • Understanding transition state stabilization is crucial for chemical design.

Purpose of the Study:

  • To design and synthesize molecular rotors capable of forming intramolecular hydrogen bonds.
  • To quantify the effect of these hydrogen bonds on rotational energy barriers.
  • To elucidate the origins of transition state stabilization.

Main Methods:

  • Synthesis of molecular rotors with and without hydrogen bonding capabilities.
  • Measurement of rotational barriers using experimental techniques.
  • Computational analysis including perturbation theory and energy decomposition analysis.

Main Results:

  • Hydrogen bonding rotors exhibited a significantly reduced rotational barrier (9.9 kcal mol⁻¹) compared to controls.
  • The observed stabilization was substantially greater than the independently measured hydrogen bond strength.
  • Computational analysis indicated a reduction in the repulsive component of the hydrogen bond interaction.

Conclusions:

  • A single intramolecular hydrogen bond can stabilize the transition state beyond its intrinsic interaction energy.
  • The rigid framework of molecular rotors effectively preorganizes functional groups for enhanced stabilization.
  • This principle has potential applications in designing efficient catalysts and understanding enzyme catalysis.