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Ionic liquids of superior thermal stability. Validation of PPh 4 + as an organic cation of impressive thermodynamic durability

https://doi.org/10.1039/D0RA03220D

Soltani, Mohammad ; McGeehee, Jimmie L. ; Stenson, Alexandra C. ; O'Brien, Richard A. ; Duranty, Edward R. ; Salter, E. Alan ; Wierzbicki, Andrzej ; Glover, T. Grant ; Davis, James H. ( May 2020 , RSC Advances)

Recent work by Wasserscheid, et al. suggests that PPh 4 + is an organic molecular ion of truly exceptional thermal stability. Herein we provide data that cements that conclusion: specifically, we show that aliphatic moieties of modified PPh 4 + -based cations incorporating methyl, methylene, or methine C–H bonds burn away at high temperatures in the presence of oxygen, forming CO, CO 2 , and water, leaving behind the parent ion PPh 4 + . The latter then undergoes no further reaction, at least below 425 °C.
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Unorthodox crystalline drug salts via the reaction of amine-containing drugs with CO 2

https://doi.org/10.1039/C9CC06429J

Soltani, Mohammad ; Mash, Brandon L. ; Henseler, Julian ; Badri, Sharhzad ; Zeller, Matthias ; Salter, E. Alan ; Wierzbicki, Andrzej ; Stenson, Alexandra C. ; Davis, James H. ( November 2019 , Chemical Communications)

Drugs containing amine groups react with CO 2 to form crystalline ammonium carbamates or carbamic acids. In this approach, both the cation and anion of the salt, or the neutral CO 2 adduct, are derived from the parent drug, generating new crystalline versions in a ‘masked’ or prodrug form. It is proposed that this approach may serve as a valuable new tool in engineering the physical properties of drugs for formulation purposes.
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