Selective Phase Transfer Reagents (OxP‐crowns) for Chromogenic Detection of Nitrates Especially Ammonium Nitrate

Chahal, Mandeep K.; Payne, Daniel T.; Labuta, Jan; Karr, Paul A.; D'Souza, Francis; Ariga, Katsuhiko and Hill, Jonathan P. (2020). Selective Phase Transfer Reagents (OxP‐crowns) for Chromogenic Detection of Nitrates Especially Ammonium Nitrate. Chemistry – A European Journal, 26(58) pp. 13177–13183.

DOI: https://doi.org/10.1002/CHEM.202003166

Abstract

Nitrogen and phosphorus-containing ions such as ammonium, nitrates and phosphates are anthropogenic pollutants while ammonium nitrate may be diverted for nefarious purposes in improvised explosive devices. Crown ether-oxoporphyrinogen conjugates (OxP-crowns) are used to selectively detect nitrates, especially their ion pairs with K+ and NH4+, based on ion pair complexation of OxP-crowns under phase transfer conditions. The presence of phosphate and carbonate lead to deprotonation of OxP-crowns. OxP-1N18C6 is capable of extracting ion pairs with nitrate from aqueous phase leading to a selective chromogenic response. Deprotonation of the OxP moiety leads to [OxP−]-1N18C6[K+] and is promoted by crown ether selective cation binding coupled with hydration of basic oxoanions, which are constrained to remain in the aqueous phase. This work illustrates the utility of molecular design to exploit partitioning and ion hydration effects establishing the selectivity of the chromogenic response.

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