References
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- Kharasch , N. , Potempa , S. J. and Wehrmeister , H. L. 1946 . Chem. Rev. , 39 : 269
- Parker , A. J. and Kharasch , N. 1959 . Chem. Rev. , 59 : 583
- Danehy , J. P. and Hunter , W. E. 1967 . J. Org. Chem. , 32 : 2047
- Ellman , G. L. 1959 . Arch. Biochem. Biophys. , 82 : 70
- Riddles , P. W. , Blakeley , R. L. and Zerner , B. 1979 . Analyt. Biochem. , 94 : 75
- Parker , A. J. 1962 . Acta Chem. Scand. , 16 : 855 A broad absorption peak with a λmax of 475 nm in alkaline 80% ethanol-water was tentatively assigned to 4-nitrophenylsulfenate ion by
- Danehy and Parameswaran8 apparently observed a deep red color upon dissolving bis(4-nitrophenyl) disulfide in 80% (v/v) dioxane (0.125 M in NaOH) at 35.2°C. They incorrectly ascribed this color to 4-nitrothiophenoxide ion, which is actually yellow in this solution
- Danehy , J. P. and Parameswaran , K. N. 1968 . J. Org. Chem. , 33 : 568
- In the absence of EDTA, the first half-life of decrease in A 550 in 3.0 M NaOH in oxygen-depleted solutions is ∼10 min. An isosbestic point occurs at 353 ± 2 nm during the oxidation of (4a) to (3a), independently of whether or not oxygen is deliberately supplied to hasten the oxidation. In the presence of 3.2 × 10−5 M EDTA the first half-life is as long as ∼40 min. in oxygen-depleted solutions. Also, it appears that EDTA at this concentration acts as a reducing agent in 3.0 M NaOH (in the presence of oxygen) because under these conditions the final yield of thiophenoxide ion (2a) (from 1.8 × 10−5 M disulfide (1a)) is 1.26 mol per original mol of (1a)
- The loss of sulfenate ion (4a) (monitored at 550 nm where (2a) has negligible absorbance) was zero-order in (4a) for ∼3 h, by which time it had fallen to half of its initial value. When oxygen was subsequently bubbled occasionally through the solution, the rate of loss of (4a) was enhanced
- Danehy . 12 reported that “exactly” 1.50 moles of thiophenoxide ion (2a) were released from the disulfide (1a) in 0.1 M NaOH in complete accord with Eq. 1. Based solely on A 412, the apparent yield of the nitrophenoxide (2a) in the present work would be 1.43 mol per mol of (1a), if the absorption spectrum and instability of the product mixture were ignored
- Danehy , J. P. , Elia , V. J. and Lavelle , C. 1971 . J. Org. Chem. , 36 : 1003
- For the thiophenoxide (2a), ε412 = 14,150 M−1 cm−1 and ε490 = 1515 M−1 cm−1 in dilute salt solutions.5
- It follows from Eq. 6 and Table I that [(4a)]i/[(2a)], = (1 - x)/(1 + 2x) = 0.244 where the subscripts refer to the concentrations produced in the time scale of decomposition of the disulfide (1a) (ε3 min). From this, x is found to be 0.51, and the initial concentration of the sulfinate ion (3a) is calculated from the relation [(3a)]i/[(2a)]i = x/(1 + 2x)
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- Kice , J. L. and Cleveland , J. P. 1973 . J. Amer. Chem. Soc. , 95 : 104
- The slower rate of oxidation of (4a) in 0.1 M NaOH as compared with 3.0 M NaOH may well reflect a 30-fold decrease in catalytic trace impurities such as Fe3+ or Cu2+. The thiophenoxide (2a) is essentially stable to oxygen under these conditions
- Kice , J. L. and Rogers , T. E. 1974 . J. Amer. Chem. Soc. , 96 : 8009
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- Danehy , J. P. 1971 . Int. J. Sulfur Chem., B. , 6 : 103
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- Oae , S. , Nomura , R. , Yoshikawa , Y. and Tagaki , W. 1969 . Bull. Chem. Soc. Japan. , 42 : 2903
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- The mechanism in Eq. (7) was proposed for the decomposition of the sulfenate ion from (7)22a on the basis of virtually uninterpretable kinetic studies (e.g., variable ionic strength and undetermined products)
- Givens , E. N. and Kwart , H. 1968 . J. Amer. Chem. Soc. , 90 : 378
- Burawoy , A. and Chaudhuri , A. 1956 . J. Chem. Soc. , : 653 Azobenzene-2-sulfenate ion:
- Putnam , R. E. and Sharkey , W. H. 1957 . J. Amer. Chem. Soc. , 79 : 6526 2,4-Dinitrobenzenesulfenate ion
- Bruice , T. C. and Markiw , R. T. 1957 . J. Amer. Chem. Soc. , 79 : 3150 Anthraquinone-1,4-disulfenate ion
- Vinkler , E. , Klivényi , F. , Lazar , J. and Kozakiewicz , I. 1969 . Acta Chim. (Budapest) , 60 : 167 Benzenesulfenate ion
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- An intramolecular hydrogen bond2a would at best be strained if the —SOH group in these aromatic sulfenic acids has the geometry found in methanesulfenic acid29 or in the —SOCH3 group in methyl 2-nitrobenzenesulfenate.30
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- Aromatic sulfenic acids are not stable when produced by pyrolysis of N-alkylidenearenesulfinamides (sulfinamines) in refluxing oxygen-free benzene.27
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- An azetidine sulfenic acid derived from a penicillin sulfoxide is stable in the crystalline form. In solution, both the sulfenic acid and its conjugate base undergo facile intramolecular reactions.36
- Chou , T. S. , Burgtorf , J. R. , Ellis , A. L. , Lammert , S. R. and Kukolja , S. P. 1974 . J. Amer. Chem. Soc. , 96 : 1609
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