A receptor able to selectively bind a phosphatidylglycerol (PPG) head group is an attractive synthetic target as a modular component of an antimicrobial therapeutic. The major challenge to the preparation of such receptors, able to exclusively recognize this bacterial membrane component, is to create a binding motif that will complex a phosphorus anion, along with hydroxyl functionality, strongly and selectively in an aqueous environment. Herein we report the synthesis and binding studies of a family of charged hydrogen bonding receptors, with phosphate anion and with PPG anion monitored with proton NMR spectroscopy and Isothermal Calorimetry (ITC) to reveal the best fit with the anionic phosphate head group of the PPG.