Arene Interactions With Nonmetallic Cations

Ammonium (R4N+), phosphonium (R4P+), sulfonium (R3S+), and some others are common in nonmetallic cations. Their chemistry is both extensive and important. From the biological perspective, however, ammonium cations are the most important of these. The amine side chain of lysine (Lys, K) is protonated at physiologic pH as is the guanidinium residue of arginine (Arg, R). The potential of nonmetallic cations to interact with arenes was recognized in the early 1980s. Meot-Ner and Deakyne[17] used mass spectrometric studies to explore the interaction between -onium salts and arenes. At about the same time, Burley and Petsko[18] surveyed the Protein Data

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