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Article Dans Une Revue Journal of Physical Chemistry A Année : 2013

Experimental and Theoretical Charge Density Analysis of a Bromoethyl Sulfonium Salt

Résumé

Bromoethyl sulfonium trifluoromethanesulfonate is a salt complex in which a sulphur atom makes three covalent bonds. This molecule has been proved to act as an efficient annulation reagent which results in the formation of synthetically challenging and pharmaceutically important 4-, 5-, 6-and 7-membered heterocycles in excellent yields. The charge density of the molecule was determined from both experimentally and theoretically derived diffraction data. The stereochemistry and electron density topology of the sulfonium group was analysed. To understand the chemical reactivity of the molecule, the electrostatic potential difference between the two carbon atoms of the bromoethyl group was investigated. It has been considered that the hydrogen atoms on the carbon atom bound to sulphur are more acidic in character due to their vicinity with the triply covalently bonded positively charged sulphur atom. The electropositivity of the S-attached and Br-attached methylene groups are compared in the experimental and theoretical charge densities using topological atomic charges and electrostatic potential at the molecular surface.
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Dates et versions

hal-02477667 , version 1 (13-02-2020)

Identifiants

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Maqsood Ahmed, Muhammad Yar, Ayoub Nassour, Benoît Guillot, Claude Lecomte, et al.. Experimental and Theoretical Charge Density Analysis of a Bromoethyl Sulfonium Salt. Journal of Physical Chemistry A, 2013, 117 (51), pp.14267-14275. ⟨10.1021/jp410301d⟩. ⟨hal-02477667⟩
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