ALKYLATING AGENTS CONTAINING A QUARTERNARY NITROGEN GROUP (1); RELATIVE NUCLEOPHILICITY METHYLATION OF ANIONS IN AQUEOUS MEDIA (2)
EDGEWOOD ARSENAL ABERDEEN PROVING GROUND MD
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A series of 18 new, water-soluble alkylating agents was synthesized. The structures contain an allkylsulfonate group as the alkylating function and a quarternary ammonium salt group attached to a hydrocarbon backbone. Alkylation rate data were obtained for 16 anion nucleophiles in aqueous media at 25C and 37C and constant salt concentration using 1-methyl-3-methylsulfonate pyridinium perchlorate as the alkylating agent substrate. The data at 25C are presented in terms of log k2kw and the Swain and Scott equation is employed to obtain the substrate constant, s 0.715. Nucleophilic constants, n, are calculated and compared with published values for 12 anions, and new constants were determined for four phosphonate ion species.
- Organic Chemistry