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Related Concept Videos

SN2 Reaction: Transition State02:26

SN2 Reaction: Transition State

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...
E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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
UV–Vis Spectroscopy: Molecular Electronic Transitions01:16

UV–Vis Spectroscopy: Molecular Electronic Transitions

In Ultraviolet–Visible (UV–Vis) spectroscopy, the absorption of electromagnetic radiation is used to probe the electronic structure of molecules. This technique provides insights into molecular electronic transitions, particularly the movement of electrons between different molecular orbitals. Radiation is absorbed if the energy of the electromagnetic radiation passing through the molecule is precisely equal to the energy difference between the excited and ground states. During this process,...
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

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Effect of Bending on the Electrical Characteristics of Flexible Organic Single Crystal-based Field-effect Transistors
08:43

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Electron transfer within 2,7-dinitronaphthalene radical anion.

Stephen F Nelsen1, Michael N Weaver, Asgeir E Konradsson

  • 1Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, WI 53706-1396, USA. nelsen@chem.wisc.edu

Journal of the American Chemical Society
|November 26, 2004
PubMed
Summary

Intramolecular electron transfer in 2,7-dinitronaphthalene radical anion occurs rapidly, with rate constants up to 10^9 s^-1. Marcus-Hush theory successfully describes this process, ruling out electron-hopping mechanisms.

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Area of Science:

  • Physical Chemistry
  • Spectroscopy
  • Quantum Chemistry

Background:

  • Investigating intramolecular electron transfer (IET) is crucial for understanding charge transport in molecular systems.
  • The 2,7-dinitronaphthalene radical anion serves as a model system for studying IET dynamics.

Purpose of the Study:

  • To determine the rate constant of intramolecular electron transfer in 2,7-dinitronaphthalene radical anion.
  • To evaluate the applicability of Marcus-Hush theory in describing the observed electron transfer dynamics.
  • To compare experimental findings with theoretical calculations for structural and energetic properties.

Main Methods:

  • Generation of 2,7-dinitronaphthalene radical anion via sodium amalgam reduction in various nitrile solvents.
  • Optical spectroscopy to observe the intervalence charge-transfer (IVCT) band.
  • Electron spin resonance (ESR) spectroscopy to measure electron transfer rate constants.
  • Ultraviolet-visible (UHF) and semiempirical AM1 calculations with configuration interaction and solvent models.

Main Results:

  • An IVCT band was observed at 1070 nm, indicating efficient intramolecular electron transfer.
  • Electron spin resonance (ESR) measurements yielded an interpolated rate constant of 3.1 x 10^9 s^-1 at 293 K.
  • Marcus-Hush theory accurately predicted rate constants, supporting a non-hopping electron transfer mechanism.
  • Theoretical calculations predicted a planar, unsymmetrical structure and highlighted the dominance of solvent reorganization energy.

Conclusions:

  • The study confirms rapid intramolecular electron transfer in 2,7-dinitronaphthalene radical anion, consistent with classical Marcus-Hush theory.
  • The findings preclude an electron-hopping mechanism, emphasizing the importance of intramolecular dynamics.
  • Computational results provide insights into the molecular structure and energy landscape governing electron transfer.