Chromatography Forum

Hellow ,

can any one tell me that this n-methyl pyrrolidone shows the keto enol tautomerism if we analyse this on RP-HPLC
Our mobile phase is ACN(0.1% H3PO4) : Water (0.1% H3PO4) .
Our main question again this can this n-methyl pyrrolidon shows keto-enol tautomerim or not

Thanks in advance

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NMP like most other amides strongly favors the keto form. As a secondary amide, the enol form would be a zwitterion, making it even more unfavorable.

Hellow sir i agree with u but in acidic media this keto form change in enol form and eluted earlier and have +ive charged on nitrogen . Is it possible

Plz reply me

thanks

praveen

Amides are extremely weak bases, and to significantly protonate them, you would need conditions that are destructive both to the amide and to most HPLC columns.