Formation and stability of the 4-methoxyphenonium ion in aqueous solution.
The reaction of 2-methoxyphenylethyl tosylate (MeO-1-Ts) is first-order in [N(3)(-)]. A carbon-13 NMR analysis of the products of the reactions of MeO-1-[α-(13)C]Ts shows the formation of MeO-1-[β-(13)C]OH and MeO-1-[β-(13)C]N(3) from the trapping of a symmetrical 4-methoxyphenonium ion reaction intermediate 2(+). An analysis of the rate and product data provides a value of k(az)/k(s) = 83 M(-1) for partitioning of 2(+) between addition of azide ion and solvent. These data set a limit for the lifetime of 2(+) in aqueous solution.
Department of Biochemistry and Applied Chemistry, Kurume National College of Technology, Komorinomachi, Kurume 830-8555, Japan.
Yutaka
Y
Tsuji
Daisuke
D
Hara
Rui
R
Hagimoto
John P
JP
Richard
D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007477:Ions / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*; D012996:Solutions; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
C570824:4-methoxyphenonium; D001593:Benzyl Compounds; D007477:Ions; D009861:Onium Compounds; D012996:Solutions; D014867:Water