Photolysis of ortho-nitrobenzylic derivatives: the importance of the leaving group

Quantum yields for the photoinduced release of seven different commonly used leaving groups (LGs) from the o -nitroveratryl protecting group were measured. It was found that these quantum yields depend strongly on the nature of the LGs. We show that the quantum efficiency with which the LGs are rele...

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Published inPhotochemical & photobiological sciences Vol. 11; no. 3; pp. 548 - 555
Main Authors Šolomek, Tomáš, Mercier, Sébastien, Bally, Thomas, Bochet, Christian G.
Format Journal Article
LanguageEnglish
Published Cham Springer International Publishing 01.03.2012
Springer Nature
Subjects
Biochemistry
Biochemistry & Molecular Biology
Biomaterials
Biophysics
Chemistry
Chemistry, Physical
Free Radicals - chemical synthesis
Free Radicals - chemistry
Life Sciences & Biomedicine
Molecular Structure
Nitrobenzenes - chemical synthesis
Nitrobenzenes - chemistry
Photolysis
Physical Chemistry
Physical Sciences
Plant Sciences
Quantum Theory
Science & Technology
DENSITY FUNCTIONALS
ETHERS
BOND-DISSOCIATION
2-NITROBENZYL COMPOUNDS
PHOTORELEASE
PHOTOCHEMICAL-REACTION MECHANISMS
PROTECTING GROUPS
REARRANGEMENTS
2-NITROTOLUENE
MOLECULES
Online AccessGet full text
ISSN1474-905X
1474-9092
1474-9092
DOI10.1039/c1pp05308f

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Abstract Quantum yields for the photoinduced release of seven different commonly used leaving groups (LGs) from the o -nitroveratryl protecting group were measured. It was found that these quantum yields depend strongly on the nature of the LGs. We show that the quantum efficiency with which the LGs are released correlates with the stabilization that these LGs provide to o -nitrobenzyl-type radicals because radical stabilizing groups weaken the C–H bond that is cleaved in the photoinduced hydrogen atom transfer step, and hence lower the barrier for this process. At the same time these substituents lower the endothermicity of the thermal hydrogen atom transfer and thus increase the barrier for the reverse process, thereby enhancing the part of the initially formed aci -nitro intermediates which undergo cyclization (which ultimately leads to LG release). Radical stabilization energies computed by DFT methods are thus a useful predictor of the relative efficiency with which LGs are photoreleased from o -nitrobenzyl protecting groups.
AbstractList Quantum yields for the photoinduced release of seven different commonly used leaving groups (LGs) from the o-nitroveratryl protecting group were measured. It was found that these quantum yields depend strongly on the nature of the LGs. We show that the quantum efficiency with which the LGs are released correlates with the stabilization that these LGs provide to o-nitrobenzyl-type radicals because radical stabilizing groups weaken the C-H bond that is cleaved in the photoinduced hydrogen atom transfer step, and hence lower the barrier for this process. At the same time these substituents lower the endothermicity of the thermal hydrogen atom transfer and thus increase the barrier for the reverse process, thereby enhancing the part of the initially formed aci-nitro intermediates which undergo cyclization (which ultimately leads to LG release). Radical stabilization energies computed by DFT methods are thus a useful predictor of the relative efficiency with which LGs are photoreleased from o-nitrobenzyl protecting groups.
Quantum yields for the photoinduced release of seven different commonly used leaving groups (LGs) from the o-nitroveratryl protecting group were measured. It was found that these quantum yields depend strongly on the nature of the LGs. We show that the quantum efficiency with which the LGs are released correlates with the stabilization that these LGs provide to o-nitrobenzyl-type radicals because radical stabilizing groups weaken the C-H bond that is cleaved in the photoinduced hydrogen atom transfer step, and hence lower the barrier for this process. At the same time these substituents lower the endothermicity of the thermal hydrogen atom transfer and thus increase the barrier for the reverse process, thereby enhancing the part of the initially formed aci-nitro intermediates which undergo cyclization (which ultimately leads to LG release). Radical stabilization energies computed by DFT methods are thus a useful predictor of the relative efficiency with which LGs are photoreleased from o-nitrobenzyl protecting groups.Quantum yields for the photoinduced release of seven different commonly used leaving groups (LGs) from the o-nitroveratryl protecting group were measured. It was found that these quantum yields depend strongly on the nature of the LGs. We show that the quantum efficiency with which the LGs are released correlates with the stabilization that these LGs provide to o-nitrobenzyl-type radicals because radical stabilizing groups weaken the C-H bond that is cleaved in the photoinduced hydrogen atom transfer step, and hence lower the barrier for this process. At the same time these substituents lower the endothermicity of the thermal hydrogen atom transfer and thus increase the barrier for the reverse process, thereby enhancing the part of the initially formed aci-nitro intermediates which undergo cyclization (which ultimately leads to LG release). Radical stabilization energies computed by DFT methods are thus a useful predictor of the relative efficiency with which LGs are photoreleased from o-nitrobenzyl protecting groups.
Quantum yields for the photoinduced release of seven different commonly used leaving groups (LGs) from the o -nitroveratryl protecting group were measured. It was found that these quantum yields depend strongly on the nature of the LGs. We show that the quantum efficiency with which the LGs are released correlates with the stabilization that these LGs provide to o -nitrobenzyl-type radicals because radical stabilizing groups weaken the C–H bond that is cleaved in the photoinduced hydrogen atom transfer step, and hence lower the barrier for this process. At the same time these substituents lower the endothermicity of the thermal hydrogen atom transfer and thus increase the barrier for the reverse process, thereby enhancing the part of the initially formed aci -nitro intermediates which undergo cyclization (which ultimately leads to LG release). Radical stabilization energies computed by DFT methods are thus a useful predictor of the relative efficiency with which LGs are photoreleased from o -nitrobenzyl protecting groups.
Author Mercier, Sébastien
Bochet, Christian G.
Šolomek, Tomáš
Bally, Thomas
Author_xml – sequence: 1
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  surname: Šolomek
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  surname: Mercier
  fullname: Mercier, Sébastien
  organization: Department of Chemistry, University of Fribourg, Current address: Syngenta Crop Protection AG
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  givenname: Thomas
  surname: Bally
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  email: Thomas.Bally@unifr.ch
  organization: Department of Chemistry, University of Fribourg
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  givenname: Christian G.
  surname: Bochet
  fullname: Bochet, Christian G.
  email: Christian.Bochet@unifr.ch
  organization: Department of Chemistry, University of Fribourg
BackLink https://www.ncbi.nlm.nih.gov/pubmed/22237825$$D View this record in MEDLINE/PubMed
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Issue 3
Keywords DENSITY FUNCTIONALS
ETHERS
BOND-DISSOCIATION
2-NITROBENZYL COMPOUNDS
PHOTORELEASE
PHOTOCHEMICAL-REACTION MECHANISMS
PROTECTING GROUPS
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MOLECULES
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PublicationTitle Photochemical & photobiological sciences
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Springer Nature
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Snippet Quantum yields for the photoinduced release of seven different commonly used leaving groups (LGs) from the o -nitroveratryl protecting group were measured. It...
Quantum yields for the photoinduced release of seven different commonly used leaving groups (LGs) from the o-nitroveratryl protecting group were measured. It...
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SubjectTerms Biochemistry
Biochemistry & Molecular Biology
Biomaterials
Biophysics
Chemistry
Chemistry, Physical
Free Radicals - chemical synthesis
Free Radicals - chemistry
Life Sciences & Biomedicine
Molecular Structure
Nitrobenzenes - chemical synthesis
Nitrobenzenes - chemistry
Photolysis
Physical Chemistry
Physical Sciences
Plant Sciences
Quantum Theory
Science & Technology
Title Photolysis of ortho-nitrobenzylic derivatives: the importance of the leaving group
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https://www.ncbi.nlm.nih.gov/pubmed/22237825
https://www.proquest.com/docview/926154621
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