Supporting information Gas-Phase Amidation of Carboxylic Acids with Woodward’s Reagent K Ions Zhou Peng , Alice L. Pilo, Carl A. Luongo and Scott A. McLuckey* Department of Chemistry Purdue University West Lafayette, Indiana, USA 47907-2084 Running title: Gas-phase Amidation of Carboxylic Acids *Address reprint requests to: Dr. S. A. McLuckey 560 Oval Drive Department of Chemistry Purdue University West Lafayette, IN 47907-2084, USA Phone: (765) 494-5270 Fax: (765) 494-0239 E-mail: mcluckey@purdue.edu 1 Figure S1. Product ion spectra derived from (a) ion/ion reaction between [ARAAARA+2Na]2+ and [wrkH]-, and (b) CID of [ARAAARA+wrk+2Na-H]+ complex. (Lightning bolt denotes ions subjected to collisional activation. Circles (°) denote water losses.) 2 Figure S2. Product ion spectra derived from CID of (a) [AKAAAKA+wrk+H]+ complex, and (b) [AKAAARA+wrk+H]+ complex. (Lightning bolt denotes ions subjected to collisional activation. Circles (°) denote water losses.) 3 Figure S3. Product ion spectra derived from (a) ion/ion reaction between [RARARAA+3H]3+ and [wrkH]-, and (b) CID of [RARARAA+wrk+2H]2+ complex. (Lightning bolt denotes ions subjected to collisional activation. Asterisks (*) denote ammonia losses whereas circles (°) denote water losses.) 4 Figure S4. Product ion spectra derived from CID of (a) [LKRApYLG+wrk+H]+ complex, and (b) [LKRApYGL-CONH2+wrk+H]+ complex. (Lightning bolt denotes ions subjected to collisional activation. Circles (°) denote water losses.) 5 Figure S5. Product ion spectra derived from CID of (a) [EPMIGVNEQLAYFYPELFR+27+H]+ and (b) [GLSDGEWQQVLNVWGK+27+H]+ (Lightning bolt denotes ions subjected to collisional activation. Asterisks (*) denote ammonia losses whereas circles (°) denote water losses) 6 Figure S6. Product ion spectra derived from (a) ion/ion reaction between [AADAADAA-2H]2- and [wrk+H]+, and (b) CID of [AADAADAA+wrk-H]- complex. (Lightning bolt denotes ions subjected to collisional activation. Circles (°) denote water losses.) 7