DOI QR코드

DOI QR Code

Spectrophotometric Study of the Interaction between Tetraethylammonium Halides and Aza-15-crown-5 with I2 and ICl in Acetonitrile Solution

  • 발행 : 2006.06.20

초록

The interaction between tetraethylammonium chloride (TEACl) with ICl and tetraethylammonium iodide (TEAI) and aza-15-crown-5 (A15C5) with $I_2$ and ICl have been examined spectrophotometrically in acetonitrile solution. The results of TEACl-ICl indicate the formation of $ICl_2$ - through equilibrium reaction. In the case of TEAI-$I_2$ and A15C5-$I_2$, the equilibrium formation of $I_3$ - is confirmed. The interaction of TEAI-ICl begins with the simultaneous production of $I_2$ and IC$I_2$ - (at TEAI/ICl < 0.5) as well as continues with the simultaneous consumption of $I_2$ and formation of I$I_3$ - (at TEAI/ICl > 0.5). Similar behavior is also observed for A15C5-ICl system. However, the changes are seen at A15C5/ICl mole ratios less and more than 0.66. Several equations have been suggested for the formation of detected species. The formation constants of various reactions were evaluated from the computer fitting of the absorbance-mole ratio data. IR spectra of A15C5 and 1:1 A15C5:ICl or A15C5:$I_2$ complexes are compared and the effect of complexation on absorption bands is discussed.

키워드

참고문헌

  1. Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 2945
  2. Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017 https://doi.org/10.1021/ja01002a035
  3. Pedersen, C. J. Fed. Proc., Fed. Am. Soc. Expl. Biol. 1968, 27, 1305
  4. Pedersen, C. J. Angew. Chem. 1988, 100, 1053 https://doi.org/10.1002/ange.19881000805
  5. Pedersen, C. J. J. Am. Chem. Soc. 1970, 92, 391 https://doi.org/10.1021/ja00705a606
  6. Pedersen, C. J. J. Org. Chem. 1971, 36, 1690 https://doi.org/10.1021/jo00811a027
  7. Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 2495 https://doi.org/10.1021/ja00986a052
  8. Pedersen, C. J. J. Am. Chem. Soc. 1970, 92, 386 https://doi.org/10.1021/ja00705a605
  9. Pedersen, C. J.; Freusdorff, H. J. Angew. Chem., Int. Ed. Engl. 1971, 83, 439 https://doi.org/10.1002/ange.19710831208
  10. Christensen, J. J.; Hill, J. O.; Izatt, R. M. Science 1971, 29, 439
  11. Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L. Chem. Rev. 1991, 91, 1721 https://doi.org/10.1021/cr00008a003
  12. Shamsipur, M.; Semnani, A.; Mokhtarifard, M. Iranian J. Chem. & Chem. Eng. 1994, 18, 193
  13. Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L.; Tarbet, B. S. Chem. Rev. 1992, 92, 1261 https://doi.org/10.1021/cr00014a005
  14. Semnani, A.; Shamsipur, M. J. Chem. Soc., Dalton Trans. 1996, 2215
  15. Semnani, A.; Shamsipur, M. Polish J. Chem. 1997, 71, 134
  16. Semnani, A.; Shareghi, B.; Sovizi, M. R. Iranian J. Chem. & Chem. Eng. 2000, 19, 67
  17. Semnani, A.; Pouretedal, H. R.; Nazari, B.; Firooz, A. Scientia Iranica 2003, 10, 317
  18. Semnani, A.; Pouretedal, H. R.; Shareghi, B. Iranian J. Chem. & Chem. Eng. 2004, 23, 1
  19. Semnani, A.; Pouretedal, H. R.; Nazari, B.; Firooz, A. Iranian J. Chem. & Chem. Eng. 2004, 23, 27
  20. Pouretedal, H. R.; Semnani, A.; Keshavarz, M. H.; Firooz, A. Asian J. Chem. 2005, 17, 329
  21. Pouretedal, H. R.; Semnani, A.; Keshavarz, M. H.; Firooz, A. Turkish J. Chem. 2005, 29, 647
  22. Beck, M. T.; Nagypal, I. Chemistry of Complex Equilibria; John Wiley & Sons: New York, U. S. A., 1990
  23. Mulliken, R. S. J. Chem. Phys. 1955, 23, 1833 https://doi.org/10.1063/1.1740588
  24. Levine, I. N. Molecular Spectroscopy; John Wiley & Sons: New York, U. S. A., 1975
  25. Schneider, H. J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry; John Wiley & Sons: New York, U. S. A., 2000
  26. Nicelly, V. A.; Dye, J. L. J. Chem. Educ. 1971, 48, 443 https://doi.org/10.1021/ed048p443
  27. Wentworth, W. E. J. Chem. Educ. 1962, 42, 162 https://doi.org/10.1021/ed042p162
  28. Powell, M. J. D. Comput. J. 1964, 7, 155 https://doi.org/10.1093/comjnl/7.2.155
  29. Rao, M.; Berne, B. J. Phys. Chem. 1981, 85, 1498 https://doi.org/10.1021/j150611a010
  30. Mulliken, R. S.; Person, W. B. Molecular Complexes; Wiley Interscience: 1969
  31. Reid, C.; Mulliken, R. S. J. Am. Chem. Soc. 1954, 76, 3869 https://doi.org/10.1021/ja01644a001
  32. Nour, E. M.; Shahada, L. A. Spectrochim. Acta 1988, 44A, 1277
  33. Hopkins, H. P.; Jahagirdar, D. V.; Windler, F. J. Phys. Chem. 1978, 82, 1254 https://doi.org/10.1021/j100500a012
  34. Mizuno, M.; Tanaka, J.; Harada, I. J. Phys. Chem. 1981, 85, 1789 https://doi.org/10.1021/j150613a006
  35. Pouretedal, H. R.; Semnani, A.; Nazari, B.; Firooz, A. Asian J. of Chem. 2005, 17, 2159
  36. Pearson, R. G. Struc. Bonding (Berlin) 1993, 80, 1 https://doi.org/10.1007/BFb0036796
  37. Shannon, R. D. Acta Crystallogr. 1976, 32A, 751
  38. Pedersen, C. J.; Frensdorff, H. K. Angew. Chem., Int., Ed. Engl. 1972, 11, 16 https://doi.org/10.1002/anie.197200161
  39. Izatt, R. M.; Bradshaw, J. S.; Nielsen, S. A.; Lamb, J. D.; Christensen, J. J.; Sen, D. Chem. Rev. 1985, 85, 271 https://doi.org/10.1021/cr00068a003
  40. Bard, A. J.; Faulkner, L. R. Electroanalytical Methods: Fund- Amentals and Applications; John Wiley & Sons: New York, U. S. A., 1979
  41. Friedrich, H. B.; Pearson, W. B. J. Chem. Phys. 1966, 44, 2161 https://doi.org/10.1063/1.1726994
  42. Guire, S. D.; Brisse, F. Can. J. Chem. 1986, 64, 142 https://doi.org/10.1139/v86-025

피인용 문헌

  1. Intriguing Photochemistry of the Additives in the Dye-Sensitized Solar Cells vol.120, pp.49, 2016, https://doi.org/10.1021/acs.jpcc.6b08235
  2. Reaction Mechanism of Iodine-Catalyzed Michael Additions vol.82, pp.8, 2017, https://doi.org/10.1021/acs.joc.7b00445
  3. Mechanisms in Iodine Catalysis vol.24, pp.37, 2018, https://doi.org/10.1002/chem.201706136
  4. INTERACTION BETWEEN 1,3,5-TRITHIANE AND IODINE MONOBROMIDE IN HALOMETHANE SOTUTIONS vol.14, pp.3, 2006, https://doi.org/10.1515/hc.2008.14.3.205
  5. INTERACTION BETWEEN BROMINE WITH TT12C4 AND HT18C6 IN DI AND TRICHLOROMETHANE SOLUTIONS vol.14, pp.4, 2006, https://doi.org/10.1515/hc.2008.14.4.277
  6. THERMODYNAMIC STUDY OF THE COMPLEXATION OF SOME THIACROWN ETHERS AND IODINE MONOBROMIDE IN CARBON TETRACHLORIDE SOLUTION vol.14, pp.5, 2006, https://doi.org/10.1515/hc.2008.14.5.307
  7. Mechanism and Scope of the Base‐Induced Dehalogenation of (E)‐Diiodoalkenes vol.2015, pp.4, 2015, https://doi.org/10.1002/ejoc.201402992