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Formation and Reactivity of Silicon–Sulfur and Silicon–Selenium Double Bonds. The First X‐Ray Structure of a Silanethione
Author(s) -
Arya Prabhat,
Boyer Jacqueline,
Carré Francis,
Corriu Robert,
Lanneau Gérard,
Lapasset Jacques,
Perrot Myriam,
Priou Christian
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198910161
Subject(s) - electrophile , reactivity (psychology) , nucleophile , silicon , intramolecular force , sulfur , selenium , x ray , chemistry , crystallography , stereochemistry , organic chemistry , physics , catalysis , medicine , alternative medicine , pathology , quantum mechanics
Silanethione 2a and silaneselenone 2b —stabilized by intramolecular Si ← N coordination— are obtained as shown below. The X‐ray structure analysis of 2a , 1‐naphthyl instead of phenyl, reveals strong zwitterionic character, which might explain the unexpectedly low reactivity toward nucleophiles and electrophiles ( a , X = S; b , X = Se).