Resonance Description of S-Nitrosothiols: Insights into Reactivity

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• 作者：Qadir K. Timerghazin ; Gilles H. Peslherbe ; Ann M. English
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：August 2, 2007
• 年：2007
• 卷：9
• 期：16
• 页码：3049 - 3052
• 全文大小：95K
• 年卷期：v.9,no.16(August 2, 2007)
• ISSN：1523-7052

文摘

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A resonance representation of the electronic structure of S-nitrosothiols as a combination of the conventional R-S-N=O structure, a zwitterionicstructure R-S⁺=N-O^-, and a RS^-/NO⁺ ion pair is proposed. The resonance forms are employed to predict and rationalize the structural andconformational properties of RSNOs, their interaction with Lewis acids, and their overall chemical reactivity.