Geometrical Requirements for Nucleophilic Substitution at Bivalent sulfur(II) and sulfur(VI): An Application of the Endocyclic Restriction Test
Terrazas, Michael S.
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https://hdl.handle.net/2142/84501
Description
Title
Geometrical Requirements for Nucleophilic Substitution at Bivalent sulfur(II) and sulfur(VI): An Application of the Endocyclic Restriction Test
Author(s)
Terrazas, Michael S.
Issue Date
2000
Doctoral Committee Chair(s)
Beak, Peter
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Inorganic
Language
eng
Abstract
These results suggest that substitution at both bivalent sulfur(II) and sulfur(VI) through a six-membered endocyclic ring is a high energy process. Thus, substitution is preferred through a linear transition state with respect to the incoming nucleophile and leaving group. A mechanism of this type would be most consistent with the classic SN2 pathway.
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