Selenium and Sulfur in Exchange Reactions: A Comparative Study | Zendy

Daniel Steinmann | Zendy; Thomas Nauser | Zendy; Willem H. Koppenol | Zendy

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Selenium and Sulfur in Exchange Reactions: A Comparative Study

Author(s) -

Daniel Steinmann,

Thomas Nauser,

Willem H. Koppenol

Publication year - 2010

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo1011569

Subject(s) - cystamine , selenium , cysteamine , nucleophile , chemistry , electrophile , sulfur , reaction rate constant , medicinal chemistry , computational chemistry , organic chemistry , kinetics , catalysis , biochemistry , physics , quantum mechanics

Cysteamine reduces selenocystamine to form hemiselenocystamine and then cystamine. The rate constants are k(1) = 1.3 × 10(5) M(-1) s(-1); k(-1) = 2.6 × 10(7) M(-1) s(-1); k(2) = 11 M(-1) s(-1); and k(-2) = 1.4 × 10(3) M(-1) s(-1), respectively. Rate constants for reactions of cysteine/selenocystine are similar. Reaction rates of selenium as a nucleophile and as an electrophile are 2-3 and 4 orders of magnitude higher, respectively, than those of sulfur. Sulfides and selenides are comparable as leaving groups.

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