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Oxidation of Some a-Hydroxy Acids by Pyridinium Fluorochromate in Aqueous Acetic Acid Media-A Kinetic and Mechanistic Study
Corresponding Author(s) : S. Syed shafi
Asian Journal of Chemistry,
Vol. 25 No. 2 (2013): Vol 25 Issue 2
Abstract
Kinetics and mechanism of oxidation of some a-hydroxy acids i.e., glycolic acid, lactic acid or mandelic acid by pyridinium fluorochromate have been studied in aqueous acetic acid medium. The main product of oxidation is oxo acids. The reaction is first order with respect to pyridinium fluorochromate, hydroxy acids and [H+]. The reaction is acid catalyzed. The oxidation of a-deuterio mandelic acid exhibits a substantial primary kinetic isotope effect (kH/kD = 5.58 at 303 K). The reaction has been studied in different percentage of acetic acid-water mixture. A suitable mechanism has been proposed
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- K.B. Wiberg, Oxidations in Organic Chemistry, Academic Press, NewYork (1965).
- E.J. Corey and D.L. Boger, Tetrahedron Lett., 28, 2461 (1978).
- N. Narayanan and T.R. Balasubramanium, J. Chem. Res (S), 336 (1991).
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- S.S. Mansoor, Asian J. Chem., 22, 7591 (2010).
- V. Dhariwal, D. Yajurvedi and P.K. Sharma, Indian J. Chem., 45A, 1158 (2006).
- A. Pandurangan, V. Murugesan and M. Palanisamy, J. Indian Chem. Soc., 72, 479 (1995).
- M.N. Bhattacharjee, M.K.Chaudhuri, H.S. Dasgupta, N. Roy and D.K. Khathing, Synthesis, 588 (1982).
- S.S. Mansoor and S.S. Shafi, Reac. Kinet. Mech. Cat., 100, 21 (2010).
- S.S. Mansoor and S.S. Shafi, J. Mol. Liq., 155, 85 (2010).
- S.S. Mansoor and S.S. Shafi, Int. J. Chem. Tech. Rech., 1, 1207 (2009).
- S.S. Mansoor and S.S. Shafi, E-J. Chem., 6, S522 (2009).
- V. Kumbhat, P.K. Sharma and K.K. Banerji, Int. J. Chem. Kinet., 34, 248 (2000).
- K.K. Sen Gupta, Int. J. Chem. Kinet., 31, 873 (1999).
- A. Goyal and S. Kothari, Bull. Chem. Soc. (Japan), 76, 2335 (2003).
- N. Nalwaya, A. Jain and B.L. Hiran, Oxid. Commun., 26, 561 (2003).
- S. Meenashisundaram and V. Sathiyendiran, Oxid. Commun., 21, 71 (1998).
- D. Garg and S. Kothari, J. Chem. Sci., 26, 333 (2004).
- N. Malani, M. Baghmar, P. Swami and P.K. Sharma, Prog. React. Kinet. Mechan., 33, 392 (2008).
- V. Sharma, P.K. Sharma and K.K. Banerji, J. Indian Chem. Soc., 74,607 (1997).
- V. Sharma, P.K. Sharma and K.K. Banerji, J. Chem. Res. (S), 290 (1996).
- G. Scatchard, Chem. Rev., 10, 229 (1932).
- G. Scatchard, J. Chem. Phys., 7, 657 (1939).
- E.S. Amis, Solvent Effects on Reaction Rates and Mechanisms,Academic Press, New York, p. 42 (1967).
- D.S. Bhuvaseshwari and K.P. Elango,Int. J. Chem. Kinet., 39, 657 (2007).
- O. Exner, Nature, 201, 488 (1964).
- O. Exner, J.R. Streitwiser and R.W. Talt, 41 Progress in Physical Organic Chemistry, John Wiley, New York (1973).
- J.F. Leffler and E. Grunwald, Rates and Equilibrium of Organic Reactions, Wiley, New York (1963).
References
K.B. Wiberg, Oxidations in Organic Chemistry, Academic Press, NewYork (1965).
E.J. Corey and D.L. Boger, Tetrahedron Lett., 28, 2461 (1978).
N. Narayanan and T.R. Balasubramanium, J. Chem. Res (S), 336 (1991).
G. Fathimajeyanthi, G. Vijayakumar and K.P. Elango, J. Serb. Chem. Soc., 67, 803 (2002).
S.S. Mansoor, Asian J. Chem., 22, 7591 (2010).
V. Dhariwal, D. Yajurvedi and P.K. Sharma, Indian J. Chem., 45A, 1158 (2006).
A. Pandurangan, V. Murugesan and M. Palanisamy, J. Indian Chem. Soc., 72, 479 (1995).
M.N. Bhattacharjee, M.K.Chaudhuri, H.S. Dasgupta, N. Roy and D.K. Khathing, Synthesis, 588 (1982).
S.S. Mansoor and S.S. Shafi, Reac. Kinet. Mech. Cat., 100, 21 (2010).
S.S. Mansoor and S.S. Shafi, J. Mol. Liq., 155, 85 (2010).
S.S. Mansoor and S.S. Shafi, Int. J. Chem. Tech. Rech., 1, 1207 (2009).
S.S. Mansoor and S.S. Shafi, E-J. Chem., 6, S522 (2009).
V. Kumbhat, P.K. Sharma and K.K. Banerji, Int. J. Chem. Kinet., 34, 248 (2000).
K.K. Sen Gupta, Int. J. Chem. Kinet., 31, 873 (1999).
A. Goyal and S. Kothari, Bull. Chem. Soc. (Japan), 76, 2335 (2003).
N. Nalwaya, A. Jain and B.L. Hiran, Oxid. Commun., 26, 561 (2003).
S. Meenashisundaram and V. Sathiyendiran, Oxid. Commun., 21, 71 (1998).
D. Garg and S. Kothari, J. Chem. Sci., 26, 333 (2004).
N. Malani, M. Baghmar, P. Swami and P.K. Sharma, Prog. React. Kinet. Mechan., 33, 392 (2008).
V. Sharma, P.K. Sharma and K.K. Banerji, J. Indian Chem. Soc., 74,607 (1997).
V. Sharma, P.K. Sharma and K.K. Banerji, J. Chem. Res. (S), 290 (1996).
G. Scatchard, Chem. Rev., 10, 229 (1932).
G. Scatchard, J. Chem. Phys., 7, 657 (1939).
E.S. Amis, Solvent Effects on Reaction Rates and Mechanisms,Academic Press, New York, p. 42 (1967).
D.S. Bhuvaseshwari and K.P. Elango,Int. J. Chem. Kinet., 39, 657 (2007).
O. Exner, Nature, 201, 488 (1964).
O. Exner, J.R. Streitwiser and R.W. Talt, 41 Progress in Physical Organic Chemistry, John Wiley, New York (1973).
J.F. Leffler and E. Grunwald, Rates and Equilibrium of Organic Reactions, Wiley, New York (1963).