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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: blackcat on October 04, 2019, 05:39:58 PM

Title: Hard Soft Acid Base theory in Organic Chemistry
Post by: blackcat 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?

Title: Re: Hard Soft Acid Base theory in Organic Chemistry
Post by: phth 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