From my (perhaps flawed) understanding...
It seems like the same general factors govern nucleophilicity (kinetic term related to reaction rate) and basicity (thermodynamic term related to acid/base equilibrium position). Of course, the same molecule can act as either a nucleophile (nucleophilic attack) and a base (abstracting a proton), depending on the reaction. (Is this right?)
But molecules can be strong nucleophiles and weak bases (e.g. I-), or weak nucleophiles and strong bases (e.g. F-). How to tell???? Especially when it seems like strong nucleophiles and strong bases both usually have the same characteristics: a negative charge, smaller atomic size, less electronegativity, less bulky (steric hindrance) and electron donating groups. Also, any other examples to clarify (since I- is the conjugate base of a strong acid, it is clearly a weak weak base)?
Thanks!
It seems like the same general factors govern nucleophilicity (kinetic term related to reaction rate) and basicity (thermodynamic term related to acid/base equilibrium position). Of course, the same molecule can act as either a nucleophile (nucleophilic attack) and a base (abstracting a proton), depending on the reaction. (Is this right?)
But molecules can be strong nucleophiles and weak bases (e.g. I-), or weak nucleophiles and strong bases (e.g. F-). How to tell???? Especially when it seems like strong nucleophiles and strong bases both usually have the same characteristics: a negative charge, smaller atomic size, less electronegativity, less bulky (steric hindrance) and electron donating groups. Also, any other examples to clarify (since I- is the conjugate base of a strong acid, it is clearly a weak weak base)?
Thanks!