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Related Concept Videos

Hydrogen Bonds01:04

Hydrogen Bonds

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...
Hydrogen Bonds00:26

Hydrogen Bonds

Hydrogen BondsHydrogen 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...
Radical Formation: Abstraction00:47

Radical Formation: Abstraction

The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...
Introduction to Chemical Bonds01:01

Introduction to Chemical Bonds

Chemical Bonds
The electrons of the outermost energy level determine the energetic stability of the atom and its tendency to form chemical bonds with other atoms. The innermost electron shell has a maximum capacity of two electrons, but the next two electron shells can each have a maximum of eight electrons. This is known as the octet rule, which states that, with the exception of the innermost shell, atoms are most stable energetically when they have eight electrons in their valence shell, the...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
¹H NMR of Labile Protons: Deuterium (²H) Substitution00:48

¹H NMR of Labile Protons: Deuterium (²H) Substitution

This lesson illustrates the role of deuterium substitution in simplifying the NMR spectrum of compounds comprising labile protons. One method employed is the use of deuterium. Amongst the three isotopes of hydrogen, deuterium (2H) has a nucleus composed of one proton and one neutron. When the D2O solvent is added to a pure dry ethanol solution, its labile proton is substituted with deuterium.

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Millisecond Hydrogen/Deuterium-Exchange Mass Spectrometry for the Study of Alpha-Synuclein Structural Dynamics Under Physiological Conditions
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Hydrogen atom donors: recent developments.

Andreas Gansäuer1, Lei Shi, Matthias Otte

  • 1Kekulé Institut für Organische Chemie und Biochemie der Universität Bonn, Germany. andreas.gansaeuer@uni-bonn.de

Topics in Current Chemistry
|April 1, 2011
PubMed
Summary
This summary is machine-generated.

New hydrogen atom transfer (HAT) reagents overcome limitations of older tin-based compounds. This review explores novel reagents and organometallic approaches for enhanced reactivity in chemical synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Classical hydrogen atom transfer (HAT) reagents, like tributyltin hydride (Bu₃SnH), present environmental and toxicity concerns.
  • Limitations of traditional HAT reagents restrict their application in certain synthetic transformations.

Purpose of the Study:

  • To review recent advancements in HAT reagents that address the drawbacks of classical group 14 reagents.
  • To highlight strategies for utilizing molecules with previously inaccessible bond dissociation energies (BDEs) as HAT reagents.
  • To discuss the emerging role of organometallic HAT reagents in modern synthesis.

Main Methods:

  • Literature review of recent developments in hydrogen atom transfer (HAT) chemistry.
  • Analysis of novel reagent design focusing on bond dissociation energy (BDE) manipulation.
  • Examination of organometallic compounds employed as HAT reagents.

Main Results:

  • Identification of new HAT reagents that offer alternatives to toxic tin-based compounds.
  • Demonstration of methods to lower the BDEs of molecules, expanding their utility in HAT reactions.
  • Overview of diverse organometallic HAT reagents and their synthetic applications.

Conclusions:

  • Emerging HAT reagents offer safer and more versatile alternatives to traditional methods.
  • Lowering BDEs and employing organometallic reagents significantly broaden the scope of HAT reactions.
  • Continued innovation in HAT reagent design promises to advance synthetic organic chemistry.