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Resonance description of S-nitrosothiols: insights into reactivity
Qadir K Timerghazin1, Gilles H Peslherbe, Ann M English
1Centre for Research in Molecular Modeling, Concordia University, 7141 Sherbrooke Street West, Montréal, Québec, Canada, H4B 1R6.
Abstract:
A resonance representation of the electronic structure of S-nitrosothiols as a combination of the conventional R-S-N=O structure, a zwitterionic structure R-S+=N-O-, and a RS-/NO+ ion pair is proposed. The resonance forms are employed to predict and rationalize the structural and conformational properties of RSNOs, their interaction with Lewis acids, and their overall chemical reactivity.
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