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Electron donors are fundamental agents in chemistry, serving as crucial participants in diverse chemical reactions across scientific disciplines. They exhibit a unique quality to contribute or share electrons, catalyzing transformations vital to biological, industrial, and environmental processes. Their significance extends from enabling biological redox reactions to fueling technological advancements in materials science and catalysis. This Wikipedia page on electron donors illuminates their multifaceted roles, exploring their mechanisms, classifications, and pervasive impact across the realms of science and technology.

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Overview

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Electron donors are fundamental components in chemistry due to their ability to readily release electrons to other atoms or molecules[1]. They are capable of providing electrons to an electron acceptor, which establishes connections between atoms and molecules, serving as a basis for the creation of compounds essential to natural and synthetic processes. Electron donors play a key role in redox (reduction-oxidation) reactions, which involve a transfer of electrons between atoms or molecules[2]. They function as "reducing agents" by supplying electrons to other substances, triggering a reduction reaction[2]. The relocation of electrons changes the oxidation states of the molecules or atoms involved, causing the electron donor to undergo oxidation, and the electron acceptor to undergo reduction[2].

In the molecular orbital diagram shown, it is clear that the hydrogen atom (left) is the electron donor because the transition energy of the electron to get to the highest occupied molecular orbital (HOMO) is lower than that of the chloride atom.

In chemical reactions involving electron donation, a complete transfer of electronic charge to an electron acceptor is not always possible. This results in a fractional transfer, which can be motivated by factors such as reversible electron transfer, the presence of unstable intermediate states, the equilibrium state of the reaction, or when the energy requirements for a full transfer are not met[3].

The ability of a molecule or atom to act as an electron donor is related to its ionization potential. The ionization potential is a measure of the energy required to remove an electron from the highest occupied molecular orbital (HOMO) of a molecule[4]. Molecules with lower ionization potential are usually better at donating electrons because their HOMO is closer in energy to the acceptor molecules. This allows the electrons to move more readily from the donor molecule to the acceptor molecule[4].

Examples

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Lewis Base

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Electron donors act as a Lewis base when they donate two paired electrons to an electron acceptor molecule. Common electron donors that are Lewis bases include molecules with lone pair rich atoms, such as anions, phosphines and amines. Following this classification, electron pair donors are nucleophiles in a chemical reaction, and will be attracted to positively charged nuclei.

Single electron donors are involved in radical formation.[5] Single electron transfers result in highly reactive products, which drive the mechanisms behind reactions such as free radical halogenation.

Biological Applications

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Water acts as an electron donor in the first step of light-based photosynthesis. The figure illustrates the two electrons, produced from water splitting, being donated into photosystem II, which is a protein complex in the electron transport chain. (Figure created using BioRender)

NADH donates its electrons into the electron transport chain,[6] to drive the process of cellular respiration. High NADH concentration results in increased amount of intracellular electrons.[7] Similar to the electron transport chain in cellular respiration, photosynthesis also has pathways for electron donation. Particularly in the light reactions of photosynthesis, water acts as an electron donor to donate electrons into the electron transport chain.[8]

Single electron donors can also be harmful in biological systems. An example of this is the superoxide anion, which is when a single electron is donated to O2. This molecule is responsible for oxidative stress.[9]

Metallic Coordination Complexes

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When two electrons are donated by the same atom to form a bond, a dative bond is created.[10] The electron donor properties of a dative bond allow bonds to be formed with electron deficient atoms, such as some electron deficient central metal atoms in coordination complexes.[11] Examples of ligands that donate two electrons to form a dative bond include carbon monoxide and phosphine.

Hydride Ion

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Since hydride ions are very electron dense, they are known for their ability to donate electrons[12]. They play a pivotal role in various chemical reactions, particularly in organic synthesis[13] and hydrogen storage catalysis[12], as they readily donate a pair of electrons to an electrophile, facilitating reduction reactions.

Alkali Metals

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Alkali metals, elements in group one of the periodic table[14], are significant electron donors due to their low ionization energies, enabling them to readily lose electrons to form cations[15]. Their electron-donating properties find extensive applications in various fields, including battery technology, organic synthesis, and catalysis. Among them, lithium, in particular, has gained substantial attention in battery research and development.


References

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  1. ^ Foster, R. (1980-08). "Electron donor-acceptor complexes". The Journal of Physical Chemistry. 84 (17): 2135–2141. doi:10.1021/j100454a006. ISSN 0022-3654. {{cite journal}}: Check date values in: |date= (help)
  2. ^ a b c Kochi, Jay K. (1967-01-27). "Mechanisms of Organic Oxidation and Reduction by Metal Complexes: Electron and ligand transfer processes form the basis for redox reactions of radicals and metal species". Science. 155 (3761): 415–424. doi:10.1126/science.155.3761.415. ISSN 0036-8075.
  3. ^ Miranda-Quintana, Ramón Alain; Ayers, Paul W. (2016). "Fractional electron number, temperature, and perturbations in chemical reactions". Physical Chemistry Chemical Physics. 18 (22): 15070–15080. doi:10.1039/C6CP00939E. ISSN 1463-9076.
  4. ^ a b Bulat, Felipe A.; Murray, Jane S.; Politzer, Peter (2021-05-01). "Identifying the most energetic electrons in a molecule: The highest occupied molecular orbital and the average local ionization energy". Computational and Theoretical Chemistry. 1199: 113192. doi:10.1016/j.comptc.2021.113192. ISSN 2210-271X.
  5. ^ Broggi, Julie; Terme, Thierry; Vanelle, Patrice (2014-01-07). "Organic Electron Donors as Powerful Single‐Electron Reducing Agents in Organic Synthesis". Angewandte Chemie International Edition. 53 (2): 384–413. doi:10.1002/anie.201209060. ISSN 1433-7851.
  6. ^ Ahmad, Maria; Wolberg, Adam; Kahwaji, Chadi I. (2023), "Biochemistry, Electron Transport Chain", StatPearls, Treasure Island (FL): StatPearls Publishing, PMID 30252361, retrieved 2023-12-06
  7. ^ Cortés-Rojo, Christian; Vargas-Vargas, Manuel Alejandro; Olmos-Orizaba, Berenice Eridani; Rodríguez-Orozco, Alain Raimundo; Calderón-Cortés, Elizabeth (2020-08-01). "Interplay between NADH oxidation by complex I, glutathione redox state and sirtuin-3, and its role in the development of insulin resistance". Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease. 1866 (8): 165801. doi:10.1016/j.bbadis.2020.165801. ISSN 0925-4439.
  8. ^ Barber, James (2017-04-03). "A mechanism for water splitting and oxygen production in photosynthesis". Nature Plants. 3 (4): 1–5. doi:10.1038/nplants.2017.41. ISSN 2055-0278.
  9. ^ Massudi, Hassina; Grant, Ross; Guillemin, Gilles J; Braidy, Nady (2012-01). "NAD + metabolism and oxidative stress: the golden nucleotide on a crown of thorns". Redox Report. 17 (1): 28–46. doi:10.1179/1351000212Y.0000000001. ISSN 1351-0002. PMC 6837626. PMID 22340513. {{cite journal}}: Check date values in: |date= (help)CS1 maint: PMC format (link)
  10. ^ Szary, Maciej J. (2023-09-01). "Dative bonding as a mechanism for enhanced catalysis on the surface of MoS2". Applied Surface Science. 630: 157462. doi:10.1016/j.apsusc.2023.157462. ISSN 0169-4332.
  11. ^ Jerabek, Paul; Schwerdtfeger, Peter; Frenking, Gernot (2019-01-05). "Dative and electron‐sharing bonding in transition metal compounds". Journal of Computational Chemistry. 40 (1): 247–264. doi:10.1002/jcc.25584. ISSN 0192-8651.
  12. ^ a b He, Teng; Cao, Hujun; Chen, Ping (2019-12). "Complex Hydrides for Energy Storage, Conversion, and Utilization". Advanced Materials. 31 (50). doi:10.1002/adma.201902757. ISSN 0935-9648. {{cite journal}}: Check date values in: |date= (help)
  13. ^ McSkimming, Alex; Colbran, Stephen B. (2013-05-28). "The coordination chemistry of organo-hydride donors: new prospects for efficient multi-electron reduction". Chemical Society Reviews. 42 (12): 5439–5488. doi:10.1039/C3CS35466K. ISSN 1460-4744.
  14. ^ "Alkali metal | Definition, Properties, & Facts | Britannica". www.britannica.com. 2023-10-15. Retrieved 2023-12-06.
  15. ^ Vinodkumar, Minaxi; Korot, Kirti; Bhutadia, Harshad (2010-06-15). "Calculations of total and ionization cross-sections on electron impact for alkali metals (Li, Na, K) from threshold to 2keV". International Journal of Mass Spectrometry. 294 (1): 54–58. doi:10.1016/j.ijms.2010.05.010. ISSN 1387-3806.