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In the synthesis of carboxylic acid derivatives (esters, amides), I often see N-hydroxysuccinimide used in conjunction with a coupling reagent (EDC, DCC). The reason given for this (from online) is that N-hydroxysuccinimide is a good leaving group.

Can anyone explain why this is so? I am unable to think of any reasons for why N-hydroxysuccinimide has a weak conjugate base compared to a general alkoxide.

Thank you.

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  • $\begingroup$ Off the top my head, having an electron-withdrawing nitrogen attached to the oxygen is going to help stabilize the negative charge on the conjugate base. $\endgroup$ – Zhe Jan 14 at 14:38
  • $\begingroup$ @Zhe but if I'm not wrong, isn't the electron donating effects of nitrogen stronger than it's electron withdrawing effects? For example how the amino group NH2 has electron donating effect rather than withdrawing. $\endgroup$ – Russell Ng Jan 14 at 15:53

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