Aqueous carbon dioxide with 2,2'-dichlorodiethylamine gives 3-(2-chloroethyl)-2-oxazolidinone. At 37°over the pH range of 6.3-7.5 and buffered with 5 X 10-4 to 170 X 10-4 M carbon dioxide, the half-lives of the pseudo-first-order reactions vary from 1.5 to 35 min. Rate and equilibrium constants bearing on the formation of the oxazolidinone have been determined. Ring closure from the carbamate anion, (CICHiCHzjzNCOz-, is the rate-controlling step, ks = 10™16 ™ 10 3 sec-1; closure from the zwitterion, (ClCHíCF^NH+COr, and reactions involving the aziridine are kinetically unimportant. The pKE of 2,2 '-dichlorodiethylamine hydrochloride, measured by pH titration and confirmed by the kinetic results, is 6.41 at 37°.(1) Support by a Sterling-Winthrop Research Fellowship and a Stauffer Chemical Fellowship is gratefully acknowledged.(2) (a) H.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.