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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
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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...
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01:26Photochemical Electrocyclic Reactions: Stereochemistry
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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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01:17Thermal Electrocyclic Reactions: Stereochemistry
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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02:30Chirality in Nature
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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
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02:05Prochirality
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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Multiscale Sampling of a Heterogeneous Water/Metal Catalyst Interface using Density Functional Theory and Force-Field Molecular Dynamics
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Chiral electrocatalysts eclipse water splitting metrics through spin control.
Aravind Vadakkayil1, Caleb Clever1, Karli N Kunzler1
1Chemistry Department, University of Pittsburgh, Pittsburgh, PA, 15260, USA.
Nature Communications
|February 24, 2023
Summary
Researchers enhanced water splitting efficiency by controlling electron spin alignment during the oxygen evolution reaction (OER). This chiral induced spin selectivity (CISS) effect improved catalyst performance beyond thermodynamic limits.
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Area of Science:
- Catalysis
- Materials Science
- Electrochemistry
Background:
- Water splitting technologies are crucial for clean energy but limited by slow oxygen evolution reaction (OER) kinetics.
- Improving OER efficiency is key to advancing technologies like hydrogen production.
Purpose of the Study:
- To enhance the efficiency of oxygen evolution reaction (OER) catalysts.
- To explore the role of spin alignment in OER catalysis using the chiral induced spin selectivity (CISS) effect.
Main Methods:
- Utilized the chiral induced spin selectivity (CISS) effect to control reaction intermediate spin alignment during electrolysis.
- Investigated chiral nanocatalysts and compared their performance to analogous achiral nanocatalysts.
Main Results:
- Achieved improved OER efficiency beyond thermodynamic considerations.
- Observed increased Faradaic efficiency and decreased reaction overpotential with chiral catalysts.
- Demonstrated a change in the rate-determining step for chiral nanocatalysts.
Conclusions:
- Spin alignment control via the CISS effect offers a novel strategy to boost OER catalyst performance.
- Catalyst spatial orientation is not required for spin selectivity, broadening applications.
- Chirality presents a transformative approach for optimizing various reaction pathways.