Computational Studies on the Sulfur Dioxide Absorption by Organic Lewis Bases

doi:10.5012/bkcs.2007.28.9.1609

Cited by 11 publications

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“…In particular, the SO 2 –pyridine dimer has been studied by many physical, − spectroscopic, ,,− and theoretical , methods. The theoretical studies by Oh et al and Shim et al were aimed at establishing the overall geometry of the SO 2 –pyridine dimerthought at the time to contain a plane of symmetryusing theoretical methods that were practical at the time (but gave the wrong answer). SO 2 –amine complexes are also of interest from a practical standpoint relating to the SO 2 -scrubbing role of amines, actual or potential, in industrial processes. − …”

Section: Introductionmentioning

confidence: 99%

“…The stability of SO 2 –amine complexes, especially tertiary amines, has allowed their detection and study with a variety of techniques. In particular, the SO 2 –pyridine dimer has been studied by many physical, − spectroscopic, ,,− and theoretical , methods. The theoretical studies by Oh et al and Shim et al were aimed at establishing the overall geometry of the SO 2 –pyridine dimerthought at the time to contain a plane of symmetryusing theoretical methods that were practical at the time (but gave the wrong answer).…”

Section: Introductionmentioning

confidence: 99%

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Sulfur Dioxide–Pyridine Dimer. FTIR and Theoretical Evidence for a Low-Symmetry Structure

Keller

2015

J. Phys. Chem. A

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Sulfur dioxide-pyridine complex formation was reinvestigated using Fourier transform infrared (FTIR) spectroscopy and computational methods. The SO2-pyridine dimer has been proposed to have a v-shaped, Cs-symmetric structure based on the microwave spectrum; however, recent research showing the occurrence of X···H-C hydrogen bonds in noncovalent complexes suggested that the structure of the complex should be re-examined. The FTIR spectrum of the dimer was obtained by numerical analysis of the spectra of pyridine-SO2 mixtures in CCl4. The spectrum showed ortho C-H stretching modes consistent with a C1-symmetric structure containing a S-O bond oriented approximately coplanar with the pyridine ring and adjacent to an ortho C-H moiety. The C1 structure, which was identified as the global minimum by various density functional theory and correlated ab initio calculations, is also consistent with the out-of-plane second moment (Pbb) value previously determined by microwave spectroscopy. The complex is converted to its mirror image via three possible Cs-symmetric transition states: v-shaped, bisected, and flat. At the M06-2X/6-311++G(2d,p) level of theory, the rotational barriers (ΔG(o‡)) are 1.40, 1.87, and 3.63 kcal mol(-1), respectively. Natural bond order analysis indicated the asymmetric complex is stabilized both by N→S donation and back-donation from O to antibonding orbitals on pyridine. Atoms in molecules calculations identified a bond critical point within the O···H-C gap consistent with a normal, albeit weak, hydrogen bond. Theoretical studies also identified a high-energy sandwich-type dimer with Cs symmetry, and a C2-symmetric SO2-pyridine2 trimer.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Sulfur Dioxide–Pyridine Dimer. FTIR and Theoretical Evidence for a Low-Symmetry Structure

Keller

2015

J. Phys. Chem. A

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Metallfreie, elektrochemische Synthese von Sulfonamiden direkt aus (Hetero)arenen, SO₂ und Aminen

et al. 2021

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zu finden. 2020 Die Autoren. Angewandte Chemie verçffentlicht von Wiley-VCH GmbH. Dieser Open Access Beitrag steht unter den Bedingungen der Creative Commons Attribution Non-Commercial NoDerivs License, die eine Nutzung und Verbreitung in allen Medien gestattet, sofern der ursprüngliche Beitrag ordnungsgemäß zitiert und nicht für kommerzielle Zwecke genutzt wird und keine ¾nderungen und Anpassungen vorgenommen werden.

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Metal‐Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO₂, and Amines

et al. 2021

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Sulfonamides are among the most important chemical motifs in pharmaceuticals and agrochemicals. However, there is no methodology to directly introduce the sulfonamide group to a non‐prefunctionalized aromatic compound. Herein, we present the first dehydrogenative electrochemical sulfonamide synthesis protocol by exploiting the inherent reactivity of (hetero)arenes in a highly convergent reaction with SO2 and amines via amidosulfinate intermediate. The amidosulfinate serves a dual role as reactant and supporting electrolyte. Direct anodic oxidation of the aromatic compound triggers the reaction, followed by nucleophilic attack of the amidosulfinate. Boron‐doped diamond (BDD) electrodes and a HFIP–MeCN solvent mixture enable selective formation of the sulfonamides. In total, 36 examples are demonstrated with yields up to 85 %.

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Computational Studies on the Sulfur Dioxide Absorption by Organic Lewis Bases

Cited by 11 publications

References 17 publications

Sulfur Dioxide–Pyridine Dimer. FTIR and Theoretical Evidence for a Low-Symmetry Structure

Sulfur Dioxide–Pyridine Dimer. FTIR and Theoretical Evidence for a Low-Symmetry Structure

Metallfreie, elektrochemische Synthese von Sulfonamiden direkt aus (Hetero)arenen, SO₂ und Aminen

Metal‐Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO₂, and Amines

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Computational Studies on the Sulfur Dioxide Absorption by Organic Lewis Bases

Cited by 11 publications

References 17 publications

Sulfur Dioxide–Pyridine Dimer. FTIR and Theoretical Evidence for a Low-Symmetry Structure

Sulfur Dioxide–Pyridine Dimer. FTIR and Theoretical Evidence for a Low-Symmetry Structure

Metallfreie, elektrochemische Synthese von Sulfonamiden direkt aus (Hetero)arenen, SO2 und Aminen

Metal‐Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO2, and Amines

Contact Info

Product

Resources

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Metallfreie, elektrochemische Synthese von Sulfonamiden direkt aus (Hetero)arenen, SO₂ und Aminen

Metal‐Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO₂, and Amines