Kinetic Studies on Tetrabutylammonium Bromochromate Oxidation of Some Mono- and Di-substituted Benzhydrols

S. Hemalatha; Basim H. Asghar; S. Sheik Mansoor

doi:10.14233/ajchem.2018.21066

Issue

Vol. 30 No. 4 (2018): Vol 30 Issue 4

Issue Published : February 28, 2018

This work is licensed under a Creative Commons Attribution 4.0 International License.

Kinetic Studies on Tetrabutylammonium Bromochromate Oxidation of Some Mono- and Di-substituted Benzhydrols

https://doi.org/10.14233/ajchem.2018.21066

S. Hemalatha

Research and Development Centre, Bharathiar University, Coimbatore-641 046, India

Basim H. Asghar

Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, P.O. Box: 9569, Makkah, Saudi Arabia

S. Sheik Mansoor

Department of Chemistry, C. Abdul Hakeem College (Autonomous), Melvisharam-632 509, India

Corresponding Author(s) : S. Sheik Mansoor

smansoors2000@yahoo.co.in

Asian Journal of Chemistry, Vol. 30 No. 4 (2018): Vol 30 Issue 4
Article Published : February 28, 2018

Abstract

The oxidation of 12 mono- and di-substituted benzhydrols (BH) by tetrabutylammonium bromochromate (TBABC) have been studied in aqueous acetic acid medium. Absence of any effect of added acrylonitrile on the reaction discounts the possibility of a one-electron oxidation, leading to the formation of free radicals. The tetrabutylammonium bromochromate oxidation of 12 mono- and di-substituted benzhydrols complies with the isokinetic relationship and Hammett relationship. The overall mechanism is proposed to involve a cyclic concerted symmetrical transition state leading to the product.

Keywords

Tetrabutylammonium bromochromate Benzhydrol Thermodynamic parameters Isokinetic relationship Kinetics

Hemalatha, S., Asghar, B. H., & Mansoor, S. S. (2018). Kinetic Studies on Tetrabutylammonium Bromochromate Oxidation of Some Mono- and Di-substituted Benzhydrols. Asian Journal of Chemistry, 30(4), 821–826. https://doi.org/10.14233/ajchem.2018.21066

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References

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G. Rajarajan, N. Jayachandramani, S. Manivarman, J. Jayabharathi and V. Thanikachalam, Transition Met.Chem., 33, 393 (2008); https://doi.org/10.1007/s11243-008-9055-1.
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B. Jagdeesh, C. Archana, M. Balaji and C. Fulchand, J. Indian Chem. Soc., 86, 481 (2009).
S.S. Mansoor and B.H. Asghar, J. Indian Chem. Soc., 90, 1395 (2013).
S.S. Mansoor and S.S. Shafi, J. Mol. Liq., 155, 85 (2010); https://doi.org/10.1016/j.molliq.2010.05.012.
S. Patel and B.K. Mishra, Int. J. Chem. Kinet., 38, 651 (2006); https://doi.org/10.1002/kin.20198.
S.S. Mansoor and S.S. Shafi, Arab. J. Chem., 8, 480 (2015); https://doi.org/10.1016/j.arabjc.2011.01.031.
A.K. Durgannavar, M.D. Meti, S.T. Nandibewoor and S.A. Chimatadar, Cogent Chem., Article: 1115210 (2015); http://dx.doi.org/10.1080/23312009.2015.1115210.
S.S. Mansoor, S.S. Shafi and S.Z. Ahmed, Arab. J. Chem., 9, S557 (2016); https://doi.org/10.1016/j.arabjc.2011.06.026.
R. Shanker and K.S. Suresh, Curr. Sci., 139, 65 (1970).
E.S. Amis, Solvent Effects on Reaction Rates and Mechanisms, Academic Press, New York, p. 42 (1967).
L.P. Hammett, Physical Organic Chemistry, McGraw-Hill, New York, edn 1 (1940).
O. Exner, J.R. Streitwiser and R.W. Talt, Progress in Physical Organic Chemistry, John Wiley, New York, p. 41 (1973).
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References

W.B. Wiberg, Oxidation in Organic Chemisry, Academic Press, New York (1995).

G. Rajarajan, N. Jayachandramani, S. Manivarman, J. Jayabharathi and V. Thanikachalam, Transition Met.Chem., 33, 393 (2008); https://doi.org/10.1007/s11243-008-9055-1.

P. Swami, D. Yajurvedi, P. Mishra and P.K. Sharma, Int. J. Chem. Kinet., 42, 50 (2010); https://doi.org/10.1002/kin.20466.

B. Sadeghy and S. Ghammami, Russ. J. Gen. Chem., 75, 1886 (2005); https://doi.org/10.1007/s11176-006-0008-0.

M. Tajbakhsh, R. Hosseinzadeh and M. Yazdani-Niaki, J. Chem. Res. (S), 508 (2002).

M. Tajbakhsh, M.M. Heravi, F. Mohanazadeh, M. Ghassemzadeh and S. Sarabi, Monatsh. Chem., 132, 1229 (2001); https://doi.org/10.1007/s007060170038.

A.R. Mahjoub, S. Ghammami and M.Z. Kassaee, Tetrahedron Lett., 44, 4555 (2003); https://doi.org/10.1016/S0040-4039(03)00989-4.

M.Z. Kassaee, S.Z. Sayyed-Alangi and H. Sajjadi-Ghotbabadi, Molecules, 9, 825 (2004); https://doi.org/10.3390/91000825.

G. Ghammamy and K. Mehrani, Afr. J. Pure Appl. Chem., 1, 8 (2007).

K.S. Rangappa, H. Ramachandra and D.S. Mahadevappa, J. Phys. Org. Chem., 10, 159 (1997); https://doi.org/10.1002/(SICI)1099-1395(199703)10:3<159::AIDPOC867>3.0.CO;2-V.

S.S. Mansoor and S.S. Shafi, React. Kinet. Mech. Catal., 100, 21 (2010); https://doi.org/10.1007/s11144-010-0148-4.

B.L. Hiran, R.K. Malkani and N. Rathore, Kinet. Catal., 46, 334 (2005); https://doi.org/10.1007/s10975-005-0081-0.

V.S. Srinivasan and N. Venkatasubramanian, Proc. Indian Acad. Sci., 87A, 219 (1978).

B. Jagdeesh, C. Archana, M. Balaji and C. Fulchand, J. Indian Chem. Soc., 86, 481 (2009).

S.S. Mansoor and B.H. Asghar, J. Indian Chem. Soc., 90, 1395 (2013).

S.S. Mansoor and S.S. Shafi, J. Mol. Liq., 155, 85 (2010); https://doi.org/10.1016/j.molliq.2010.05.012.

S. Patel and B.K. Mishra, Int. J. Chem. Kinet., 38, 651 (2006); https://doi.org/10.1002/kin.20198.

S.S. Mansoor and S.S. Shafi, Arab. J. Chem., 8, 480 (2015); https://doi.org/10.1016/j.arabjc.2011.01.031.

A.K. Durgannavar, M.D. Meti, S.T. Nandibewoor and S.A. Chimatadar, Cogent Chem., Article: 1115210 (2015); http://dx.doi.org/10.1080/23312009.2015.1115210.

S.S. Mansoor, S.S. Shafi and S.Z. Ahmed, Arab. J. Chem., 9, S557 (2016); https://doi.org/10.1016/j.arabjc.2011.06.026.

R. Shanker and K.S. Suresh, Curr. Sci., 139, 65 (1970).

E.S. Amis, Solvent Effects on Reaction Rates and Mechanisms, Academic Press, New York, p. 42 (1967).

L.P. Hammett, Physical Organic Chemistry, McGraw-Hill, New York, edn 1 (1940).

O. Exner, J.R. Streitwiser and R.W. Talt, Progress in Physical Organic Chemistry, John Wiley, New York, p. 41 (1973).

L. Liu and Q.X. Guo, Chem. Rev., 101, 673 (2001); https://doi.org/10.1021/cr990416z.

K.K. Banerji, J. Org. Chem., 53, 2154 (1988); https://doi.org/10.1021/jo00245a004.

R.B. Woodward and R. Hoffmann, Angew. Chem. Int. Ed. Engl., 8, 781 (1969); https://doi.org/10.1002/anie.196907811.

J.S. Littler, Tetrahedron, 27, 81 (1971); https://doi.org/10.1016/S0040-4020(01)92399-3

Issue

Vol. 30 No. 4 (2018): Vol 30 Issue 4

Kinetic Studies on Tetrabutylammonium Bromochromate Oxidation of Some Mono- and Di-substituted Benzhydrols

Corresponding Author(s) : S. Sheik Mansoor

Abstract

Keywords

Full Article

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