Bulletin of the Korean Chemical Society

  • 제24권2호
  • /
  • Pages.205-208
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  • 2003
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Reaction Monitoring of Imine Synthesis Using Raman Spectroscopy

  • 발행 : 2003.02.20
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초록

Laser-induced Raman spectroscopy has been utilized to demonstrate its feasibility for studying the kinetics of imine formation in chloroform solvent. The imine formation, by the nucleophilic addition of primary amine to the carbonyl group of ketone, has been monitored at ten minute intervals for eight hours. The intensity of the C=O stretching mode at 1684 $cm^{-1}$ was measured to determine the rate constant of the reaction. In order to correct the sample-to-sample fluctuations in Raman peak area, this peak was normalized to the C-Cl bending peak at 666 $cm^{-1}$. By the peak area change during the course of reaction, the second order rates at three different temperatures have been determined. The substituent effects on the π conjugations of imine product have also been investigated. On the basis of Raman frequency shifts, the delocalization properties of the aromatic system modified by substitution of a hydrogen atom with -Cl and $-CH_3O$ groups could be clearly understood.

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참고문헌

  1. Vdovenko, S. I.; Gerus, I. I.; Wojcik, J. J. Phys. Org. Chem. 2001, 14, 533. https://doi.org/10.1002/poc.390
  2. Kohler, M. A.; Richarz, W. Chem. Engng. Sci. 1985, 10, 1983.
  3. Smith, M. B.; March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structures, 5th Ed.; John Wileys & Sons, Ltd.: Chichester, UK, 2001; pp 1177-78
  4. Bruneel, J. L.; Lassegues, J. C.; Sourisseau, C. J. Raman Spectrosc. 2002, 33, 815. https://doi.org/10.1002/jrs.915
  5. Jeon, S.; Woo, J.; Kyong, J. B.; Choo, J. Bull. Korean Chem. Soc. 2001, 22, 1264.
  6. Jeon, S.; Choo, J.; Kim, S.; Kwon, Y.; Kim, J.; Lee, Y.; Chung, H. J. Mol. Struct. 2002, 609, 159. https://doi.org/10.1016/S0022-2860(01)00968-1
  7. Korovenicheva, I. K.; Furin, G. G.; Yakobson, G. G. J. Mol. Struct. 1984, 114, 395. https://doi.org/10.1016/0022-2860(84)87171-9
  8. Schmid, E. D.; Schlenker, P.; Brand, R. R. M. J. Raman Spectrosc. 1977, 6, 314. https://doi.org/10.1002/jrs.1250060610
  9. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502. https://doi.org/10.1021/jp960976r
  10. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785.
  11. Becke, A. D. J. Chem. Phys. 1993, 98, 5648. https://doi.org/10.1063/1.464913
  12. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clliford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowsski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian Inc.: Pittsburg PA, 1998.

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