433-98-7Relevant articles and documents
Molecular structure and conformations of 2-nitrobenzenesulfonyl fluoride: Gas-phase electron diffraction and quantum chemical calculations study
Petrov, Vjacheslav M.,Girichev, Georgiy V.,Oberhammer, Heinz,Giricheva, Nina I.,Bardina, Anna V.,Petrova, Valentina N.,Ivanov, Sergey N.
, p. 97 - 103 (2010)
The molecular structure and conformational properties of 2-nitrobenzenesulfonyl fluoride, 2-NO2-C6H4SO2F, have been studied by gas-phase electron diffraction (GED) and quantum chemical methods (B3LYP/6-311+G and MP2/6-31G). Quantum chemical calculations predict the existence of three conformers for 2-NO2-C6H4SO2F each of them possesses C1 symmetry. Conformer I, in which the S-F bond of the SO2F group is nearly perpendicular to the plane of benzene ring, is predicted to be most favored. Conformer II, in which the S-F bond is situated in opposite direction with reference to the NO2 group, possesses intermediate energy (Δ1-2 = 0.73 kcal/mol (B3LYP), or 0.71 kcal/mol (MP2)), and conformer III with the S-F bond tilted to the NO2 group possesses the higher energy (Δ1-3 = 1.58 kcal/mol (B3LYP), or 1.47 kcal/mol (MP2)). The analysis of the GED intensities was carried out assuming the vapour consists of three conformers. In was obtained the conformer I dominates in vapour over solid 2-NO2-C6H4SO2F at T = 383(5) K. The conformer III concentration was found to be negligible. In dominant conformer I the S-F bond is bent slightly towards the nitro group (φ(C-C-S-F) = 84(8)°), and the torsional angle of the nitro group with respect to the benzene ring φ(C-C-N-O) equals 125(4)°. The conformation properties were determined by the potential energy surface analysis. The relative stability of conformers is discussed.
Synthesis of Sulfonyl Fluorides from Sulfonamides
Pérez-Palau, Marina,Cornella, Josep
supporting information, p. 2497 - 2500 (2020/03/11)
A simple and practical synthesis of sulfonyl fluorides from sulfonamides is reported. The method capitalizes on the formation of the sulfonyl chloride by virtue of the reaction of Pyry-BF4 and MgCl2, and subsequent in situ conversion to the more robust and stable sulfonyl fluoride by the presence of KF. The mild conditions and high chemoselectivity of the protocol enable the late-stage formation of sulfonyl fluorides from densely functionalized molecules.
(Chlorosulfonyl)benzenesulfonyl Fluorides - Versatile Building Blocks for Combinatorial Chemistry: Design, Synthesis and Evaluation of a Covalent Inhibitor Library
Tolmachova, Kateryna A.,Moroz, Yurii S.,Konovets, Angelika,Platonov, Maxim O.,Vasylchenko, Oleksandr V.,Borysko, Petro,Zozulya, Sergey,Gryniukova, Anastasia,Bogolubsky, Andrey V.,Pipko, Sergey,Mykhailiuk, Pavel K.,Brovarets, Volodymyr S.,Grygorenko, Oleksandr O.
, p. 672 - 680 (2018/11/23)
Multigram synthesis of (chlorosulfonyl)benzenesulfonyl fluorides is described. Selective modification of these building blocks at the sulfonyl chloride function under parallel synthesis conditions is achieved. It is shown that the reaction scope includes the use of (hetero)aromatic and electron-poor aliphatic amines (e.g., amino nitriles). Utility of the method is demonstrated by preparation of the sulfonyl fluoride library for potential use as covalent fragments, which is demonstrated by a combination of in silico and in vitro screening against trypsin as a model enzyme. As a result, several inhibitors were identified with activity on par with that of the known inhibitor.
