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Topic: Hard Soft Acid Base theory in Organic Chemistry  (Read 2215 times)

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Offline blackcat

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Hard Soft Acid Base theory in Organic Chemistry
« on: October 04, 2019, 05:39:58 PM »
Do you think carbon-based acid (i.e. carbocation) and carbon-based base (i.e. carbanion) are usually soft?
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Offline phth

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Re: Hard Soft Acid Base theory in Organic Chemistry
« Reply #1 on: October 05, 2019, 09:57:43 PM »
What does HSAB theory principle even mean? Carbocations are hard. Carbanions are soft. Carbocations react with hard things (chloride, H2O, ...), and they react with soft things (like hydride shifts). Carbanions react with hard things (protons), and soft things (nitrile). There are blurred lines, I think a good open access review on the subject is: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201007100
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