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Gas‐phase reactions of the benzyne negative ions
Author(s) -
Wenthold Paul G.,
Hu Jun,
Squires Robert R.
Publication year - 1998
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(199809)33:9<796::aid-jms683>3.0.co;2-3
Subject(s) - aryne , chemistry , nucleophile , reactivity (psychology) , reagent , bifunctional , ion , medicinal chemistry , computational chemistry , photochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
The reactions of o ‐, m ‐ and p ‐benzyne anions and the phenide ion with a series of neutral reagents are described. The m ‐ and p ‐benzyne anions display similar behavior towards Brønsted acids, CS 2 , N 2 O, NO and O 2 , which is analogous to that of phenide ion but clearly different from that of o ‐benzyne anion. The strongly basic and nucleophilic character of m ‐ and p ‐benzyne anions dominates their reactivity, and radical‐type reactions are generally not observed. Novel bifunctional reactions between m ‐ and p ‐benzyne anions and both CS 2 and NO are observed in which two sequential S‐atom abstractions and two NO additions, respectively, take place. © 1998 John Wiley & Sons, Ltd.