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Hetero-aromatic N-base-promoted oxidation of 4-chlorobenzyl alcohol by Cr(VI) in micellar media

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Abstract

A little attempt has been made to get in touch with the green chemistry studying the successful occurrence of oxidation of 4-chlorobenzyl alcohol to 4-chlorobenzaldehyde in micellar media by Cr(VI), and its kinetics has been recorded spectrophotometrically following pseudo-first-order reaction conditions at λmax = 440 nm. In this purpose, some common hetero-aromatic bases like 2-picolinic acid, 1,10-phenanthroline and 2,2′-bipyridine have been utilized successfully for many fold rate enhancement of the reaction. Necessary spectroscopic evidences have been produced in support of the product formation.

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Abbreviations

CMC:

Critical micelle concentration

SDS:

Sodium dodecyl sulphate

SDBS:

Sodium dodecyl benzene sulphonate

CPC:

Cetylpyridinium chloride

CTAB:

Cetyltrimethylammonium bromide

bpy:

2,2′-Bipyridine

phen:

1,10-Phenanthroline

PA:

2-Picolinic acid

2,4-DNP:

2,4-Dinitrophenylhydrazine

rds:

Rate determining step

References

  1. S. Malik, D. Saha, M.H. Mondal, P. Sar, A. Ghosh, K. Mahali, B. Saha, J. Mol. Liq. 225, 207 (2017)

    CAS  Google Scholar 

  2. B. Saha, S. Sarkar, K.M. Chowdhury, Int. J. Chem. Kinet. 40, 282 (2008)

    CAS  Google Scholar 

  3. P. Bhattacharyya, A. Ghosh, B. Saha, Tenside Surf. Det. 52, 36 (2015)

    CAS  Google Scholar 

  4. A. Ghosh, P. Sar, S. Malik, B. Saha, J. Mol. Liq. 211, 48 (2015)

    CAS  Google Scholar 

  5. M.H. Mondal, S. Malik, S. De, S.S. Bhattacharyya, B. Saha, Res. Chem. Intermed. 43, 1651 (2017)

    CAS  Google Scholar 

  6. P. Sar, A. Ghosh, S. Malik, D. Ray, B. Das, B. Saha, J. Ind. Eng. Chem. 42, 53 (2016)

    CAS  Google Scholar 

  7. A. Ghosh, R. Saha, K. Mukherjee, S.K. Ghosh, B. Saha, Spectrochim. Acta Part A 109, 55 (2013)

    CAS  Google Scholar 

  8. R. Saha, S.K. Ghosh, A. Ghosh, I. Saha, K. Mukherjee, A. Basu, B. Saha, Res. Chem. Intermed. 39, 631 (2013)

    CAS  Google Scholar 

  9. B.H. Asghar, S.S. Mansoor, A.M. Hussain, V. Saleem Malik, K. Aswin, S.P.N. Sudhan, Arab. J. Chem. 10, S2115 (2017)

    CAS  Google Scholar 

  10. R. Saha, R. Nandi, B. Saha, J. Coord. Chem. 64, 1782 (2011)

    CAS  Google Scholar 

  11. B. Saha, C. Orvig, Coord. Chem. Rev. 254, 2959 (2010)

    CAS  Google Scholar 

  12. S. Malik, A. Ghosh, P. Sar, M.H. Mondal, K. Mahali, B. Saha, J. Chem. Sci. 129, 637 (2017)

    CAS  Google Scholar 

  13. S. Sundaram, P.S. Raghavan, Chromium-VI Reagents: Synthetic Applications (Springer, Heidelberg, 2011), p. 47

    Google Scholar 

  14. I.T. Horvath, Green Chem. 10, 1024 (2008)

    CAS  Google Scholar 

  15. A.K. Das, Coord. Chem. Rev. 248, 81 (2004)

    CAS  Google Scholar 

  16. T. Kitanosono, K. Masuda, P. Xu, S. Kobayashi, Chem. Rev. 118, 679 (2018)

    CAS  PubMed  Google Scholar 

  17. A. Levina, P.A. Lay, Chem. Res. Toxicol. 21, 563 (2008)

    CAS  PubMed  Google Scholar 

  18. B.H. Lipshutz, F. Gallou, S. Handa, A.C.S. Sustain, Chem. Eng. 4, 5838 (2016)

    CAS  Google Scholar 

  19. G.L. Sorella, G. Strukul, A. Scarso, Green Chem. 17, 644 (2015)

    Google Scholar 

  20. T. Dwars, E. Paetzold, G. Oehme, Angew. Chem. Int. Ed. 44, 7174 (2005)

    CAS  Google Scholar 

  21. S. Tascioglu, Tetrahedron 52, 11113 (1996)

    CAS  Google Scholar 

  22. M.L. Carreto, S. Rubio, D. Perez-Bendito, Analyst 121, 33R (1996)

    Google Scholar 

  23. M. Almgren, A. Valstar, Langmuir 15, 2635 (1999)

    Google Scholar 

  24. D. Kumar, M.A. Rub, J. Mol. Liq. 238, 389 (2017)

    CAS  Google Scholar 

  25. Y. Cheng, L. Zhao, T. Li, Soft Matter 10, 2714 (2014)

    CAS  PubMed  Google Scholar 

  26. S. Malik, A. Ghosh, B. Saha, J. Solut. Chem. 45, 109 (2016)

    CAS  Google Scholar 

  27. S. Chowdhury, A. Rakshit, A. Acharjee, B. Saha, ChemistrySelect 4, 6978 (2019)

    CAS  Google Scholar 

  28. S.H. Seo, J.Y. Chang, G.N. Tew, Angew. Chem. Int. Ed. 45, 7526 (2006)

    CAS  Google Scholar 

  29. S. Chowdhury, A. Rakshit, A. Acharjee, A. Ghosh, K. Mahali, B. Saha, J. Mol. Liq. 290, 111247 (2019)

    Google Scholar 

  30. A. Acharjee, A. Rakshit, S. Chowdhury, S. Malik, M.K. Barman, M.A. Ali, B. Saha, J. Mol. Liq. 277, 360 (2019)

    CAS  Google Scholar 

  31. S. Malik, M.H. Mondal, A. Ghosh, S. De, K. Mahali, S.S. Bhattacharyya, B. Saha, J. Solut. Chem. 45, 1043 (2016)

    Google Scholar 

  32. S.K. Ghosh, A. Basu, K.K. Paul, B. Saha, Mol. Phys. 107, 615 (2009)

    CAS  Google Scholar 

  33. P. Sar, A. Ghosh, R. Saha, B. Saha, Res. Chem. Intermed. 41, 5331 (2015)

    CAS  Google Scholar 

  34. B. Saha, Inorg. React. Mech. 6, 287 (2008)

    CAS  Google Scholar 

  35. A. Ghosh, R. Saha, B. Saha, J. Mol. Liq. 196, 223 (2014)

    CAS  Google Scholar 

  36. A. Ghosh, R. Saha, K. Mukherjee, P. Sar, S.K. Ghosh, S. Malik, S.S. Bhattacharyya, B. Saha, J. Mol. Liq. 190, 81 (2014)

    CAS  Google Scholar 

  37. A. Ghosh, K. Sengupta, R. Saha, B. Saha, J. Mol. Liq. 198, 369 (2014)

    CAS  Google Scholar 

  38. M. Budny, J. Włodarczyk, T. Muzioł, M.J. Bosiak, A. Wolan, Tetrahedron Lett. 58, 4285 (2017)

    CAS  Google Scholar 

  39. Y. Todoroki, K. Kobayashi, H. Yoneyama, S. Hiramatsu, M. Jin, B. Watanabe, M. Mizutani, N. Hirai, Bioorg. Med. Chem. 16, 3141 (2008)

    CAS  PubMed  Google Scholar 

  40. A. Majhi, S.S. Kim, H.S. Kim, Appl. Organomet. Chem. 22, 466 (2008)

    CAS  Google Scholar 

  41. S.R. Joshi, K.L. Kataria, S.B. Sawant, J.B. Joshi, Ind. Eng. Chem. Res. 44, 325 (2005)

    CAS  Google Scholar 

  42. N. Mibu, K. Yokomizo, M. Uyeda, K. Sumoto, Chem. Pharm. Bull. 51, 1325 (2003)

    CAS  PubMed  Google Scholar 

  43. Z. Karimi-Jaberi, B. Pooladian, M. Moradi, E. Ghasemi, Chin. J. Catal. 33, 1945 (2012)

    CAS  Google Scholar 

  44. C. Walling, C. Zhao, G.M. El-Taliawi, J. Org. Chem. 48, 4910 (1983)

    CAS  Google Scholar 

  45. Y. Mao, A. Bakac, J. Phys. Chem. 100, 4219 (1996)

    CAS  Google Scholar 

  46. M. Mamaghani, F. Shirini, F. Parsa, Russ. J. Org. Chem. 38, 1113 (2002)

    CAS  Google Scholar 

  47. M. Lee, S. Chang, Tetrahedron Lett. 41, 7507 (2000)

    CAS  Google Scholar 

  48. I.E. Marko, P.R. Giles, M. Tsukazaki, I. Chelle-Regnaut, A. Gautier, S.M. Brown, C.J. Urch, J. Org. Chem. 64, 2433 (1999)

    CAS  Google Scholar 

  49. M.A. Zolfigol, F. Shirini, G. Chehardoli, E. Kolvari, J. Mol. Catal. A Chem. 265, 272 (2007)

    CAS  Google Scholar 

  50. A.C. Chaskar, S.R. Bhandari, A.B. Patil, O.P. Sharma, S. Mayeker, Synth. Commun. 39, 366 (2008)

    Google Scholar 

  51. F. Shirini, M.A. Zolfigol, M. Abedini, P. Salehi, Mendeleev Commun. 13, 265 (2003)

    Google Scholar 

  52. B. Paul, D.D. Purkayastha, S.S. Dhar, Mater. Chem. Phys. 181, 99 (2016)

    CAS  Google Scholar 

  53. A. Basu, R. Saha, J. Mandal, S. Ghosh, B. Saha, J. Biomed. Sci. 3, 735 (2010)

    CAS  Google Scholar 

  54. B. Ozgun, N. Degirmenbasi, Monatsh. Chem. 135, 483 (2004)

    Google Scholar 

  55. K. Bijudas, P. Bashpa, T.D. Radhakrishnan Nair, Bull. Chem. React. Eng. Catal. 9, 142 (2014)

    Google Scholar 

  56. B. Saha, M. Islam, A.K. Das, Inorg. React. Mech. 6, 141 (2006)

    CAS  Google Scholar 

  57. A. Ghosh, R. Saha, B. Saha, J. Ind. Eng. Chem. 20, 345 (2014)

    CAS  Google Scholar 

  58. J. Clayden, N. Greeves, S. Warren, Organic Chemistry, 2nd edn. (Oxford University Press, New York, 2001), pp. 138–140

    Google Scholar 

  59. S. Caron, Practical Synthetic Organic Chemistry: Reactions, Principles, and Techniques, 1st edn. (Wiley, New Jersey, 2011), pp. 75–76

    Google Scholar 

  60. A.I. Vogel, in Textbook of practical organic chemistry, 5th edn., ed. by B.S. Furniss, A.J. Hannaford, P.W.G. Smith, A.R. Tatchell (Longman Group UK Limited, London, 1989), pp. 1257–1258

    Google Scholar 

  61. F.G. Mann, B.C. Saunders, Practical Organic Chemistry, 4th edn. (Longman, New York, 1960), p. 540

    Google Scholar 

  62. J.F. Perez-Benito, C. Arias, R.M. Rodriguez, M. Ros, New J. Chem. 22, 1445 (1998)

    CAS  Google Scholar 

  63. F.A. Cotton, G. Wilkinson, C.A. Murillo, M. Bochmann, Advanced Inorganic Chemistry, 6th edn. (Wiley, New York, 1999)

    Google Scholar 

  64. E. Perez-Benito, E. Rodenas, Langmuir 7, 232 (1991)

    CAS  Google Scholar 

  65. V. Roldan, J.C. Gonzalez, M. Santoro, S. Garcia, N. Casado, S. Olivera, J.C. Boggio, J.M. Salas-Peregrin, S. Signorella, L.F. Sala, Can. J. Chem. 80, 1676 (2002)

    CAS  Google Scholar 

  66. B.N. Figgis, Introduction to Ligand Fields (Wiley Eastern Limited, New Delhi, 1966), p. 222

    Google Scholar 

  67. Z. Khan, K. Ud-Din, Transition Met. Chem. 27, 832 (2002)

    CAS  Google Scholar 

  68. M. Islam, B. Saha, A.K. Das, J. Mol. Catal. A Chem. 266, 21 (2007)

    CAS  Google Scholar 

  69. C.K. Jorgensen, Absorption Spectra and Chemical Bonding in Complexes (Pergamon Press Ltd., Oxford, London, 1964), p. 290

    Google Scholar 

  70. S.K. Ghosh, R. Saha, A. Ghosh, K. Mukherjee, A. Basu, S.S. Bhattacharyya, B. Saha, J. Kor. Chem. Soc. 56, 720 (2012)

    CAS  Google Scholar 

  71. R. Saha, A. Ghosh, P. Sar, I. Saha, S.K. Ghosh, K. Mukherjee, B. Saha, Spectrochim. Acta Part A 116, 524 (2013)

    CAS  Google Scholar 

  72. S.K. Ghosh, A. Ghosh, R. Saha, B. Saha, Phys. Chem. Liq. 53, 146 (2015)

    CAS  Google Scholar 

  73. A. Acharjee, A. Rakshit, S. Chowdhury, I. Datta, M.K. Barman, M.A. Ali, B. Saha, J. Mol. Liq. 293, 111475 (2019)

    CAS  Google Scholar 

  74. K. Mukherjee, R. Saha, A. Ghosh, S.K. Ghosh, B. Saha, Spectrochim. Acta Part A 101, 294 (2013)

    CAS  Google Scholar 

  75. S.K. Ghosh, A. Ghosh, R. Saha, B. Saha, Tenside Surf. Det. 49, 370 (2012)

    CAS  Google Scholar 

  76. S.K. Ghosh, A. Basu, R. Saha, A. Ghosh, K. Mukherjee, B. Saha, J. Coord. Chem. 65, 1158 (2012)

    CAS  Google Scholar 

  77. P.D.T. Huibers, Langmuir 15, 7546 (1999)

    CAS  Google Scholar 

  78. V. Karikalan, A. Panneerselvam, K. Vallalperuman, Dig. J. Nanomater. Biosci. 13, 115 (2018)

    Google Scholar 

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Acknowledgements

The authors thank UGC [Grant—F.540/1/CAS-II/2016(SAP-I)], New Delhi for providing financial support.

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Authors and Affiliations

  1. Homogeneous Catalysis Laboratory, Department of Chemistry, The University of Burdwan, Golapbag, Burdwan, West Bengal, 713104, India

    Atanu Rakshit, Suman Chowdhury, Animesh Acharjee, Indukamal Datta, Satyajit Biswas, Shuvendu Sekhar Bhattacharyya & Bidyut Saha

  2. Department of Chemistry, Hooghly Mohsin College, Chinsurah, West Bengal, 712101, India

    Animesh Acharjee

  3. Department of Chemistry, IIT (ISM), Dhanbad, Jharkhand, 826004, India

    Kuheli Dome

  4. Department of Chemistry, Hooghly Women’s College, Chinsurah, West Bengal, 712103, India

    Satyajit Biswas

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  1. Atanu Rakshit
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Rakshit, A., Chowdhury, S., Acharjee, A. et al. Hetero-aromatic N-base-promoted oxidation of 4-chlorobenzyl alcohol by Cr(VI) in micellar media. Res Chem Intermed 46, 2559–2578 (2020). https://doi.org/10.1007/s11164-020-04106-x

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