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Photo-Isomerization and Decarboxilation of 2-Amino-5-Chlorobenzoic Acid in Argon Matrix

Year 2018, Volume 5, Issue 2, 55 - 63, 28.12.2018

Abstract

In this paper, the matrix isolation infrared spectroscopy technique is presented, and its application to the work of photoisomerization reaction for 2-amino-5-chlorobenzoic acid (AClBA) was studied by matrix isolation spectroscopy in argon matrix at 15 K. The considered photoreactions include conformational isomerizations as well as bond-breaking/bond-forming structural isomerizations. UV irradiation at l > 234 nm of the matrix-isolated compound was found to lead to conversion of this conformer into the other conformers and also to decarboxylation of the AClBA, producted with of CO2 and 2-amino-5-chlorobenzene (AClB). The analysis of the experimental data on matrix isolated AClBA was supported by extensive quantum chemical calculations.

References

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  • Norman, I., and Porter, G. 1954, Nature, 174, 508-509.
  • Lin, C.Y., and Krantz, A. 1972, J. Chem. Soc. Chem. Commun., 19, 1111/1112, 1316.
  • Chapman, O.L., McIntosh, C.L., and Pacansky, J. 1973, J. Am. Chem. Soc., 95, 244-246.
  • Pong, R.G.S., and Shirk, J.S. 1973, J. Am. Chem. Soc., 95, 248-249.
  • Breda, S., Reva, I., Lapinski, L., and Fausto, R. 2004, Phys. Chem. Chem. Phys., 6, 929-937.
  • Rochkind, M.M. 1967, Anal. Chem., 39, 567-574.
  • Perutz, R.N., and Turner, J.J. 1973, J. Chem. Soc., Faraday Trans. 2, 69, 452-461.
  • Barnes, A.J., Bignall, J.C., and Purnell, C.J. 1975, J. Raman Spectrosc., 4, 159.
  • Lapinski, L., Rostkowska, H., Khvorostov, A., Fausto, R., and Nowak, M.J. 2003, J. Phys. Chem. A, 107, 5913-5919.
  • Szczesniak, M., Leszczynski, J., and Person, W.B. 1992, J. Am. Chem. Soc., 114, 2731-2733.
  • Buyl, F., Smets, J., Maes, G., and Adamowicz, L. 1995, J. Phys. Chem., 99, 14967-14979.
  • Stepanian, S.G., Reva, I.D., Radchenko, E.D., Rosado, M.T.S., Duarte, M.L.T.S., Fausto, R., and Adamowicz, L. 1998, J. Phys. Chem., 102, 1041–1054.
  • Jarmelo, S., Lapinski, L., Nowak, M.J., Carey, P.R., and Fausto, R. 2005, J. Phys. Chem. A, 109, 5689.
  • Gómez-Zavaglia, A., Reva, I.D., and Fausto, R. 2003, Phys. Chem. Chem. Phys., 5, 41-51.
  • Gómez-Zavaglia, A., and Fausto, R. 2003, Vibrat. Spectrosc., 33, 105-126.
  • Stepanian, S.G., Reva, I.D., Radchenko, E.D. and Adamowicz, L. 1998, J. Phys. Chem. A, 102, 4623-4629.
  • Kaczor, A., Reva, I.D., Proniewicz, L.M., and Fausto, R. 2006, J. Phys. Chem. A, 110, 2360-2370.
  • See, for example, (a) Reva, I.D., Jarmelo, S., Lapinski, L., and Fausto, R., 2004, Chem. Phys. Lett., 389, 68. (b) Ramaekers, R., Maes, G., Adamowicz, L., and Dkhissi, A. 2001, J. Mol. Struct., 560, 205. (c) Borba, A., Gómez-Zavaglia, A., Lapinski, L., and Fausto, R. 2004, Phys. Chem. Chem. Phys., 6, 2101. (d) Sander, W., Wandel, H., Bucher, G., Grafenstein, J., Kraka, E., and Cremer, D. 1998, J. Am. Chem. Soc., 120, 8480.
  • Chapman, O.L., McIntosh, C.L., and Pacansky, J. 1973, J. Am. Chem. Soc., 95, 614-617.
  • M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, J.E. Peralta Jr, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision A.0.2, Gaussian, Inc., Wallingford CT, 2009.
  • Raghavachari K., Binkley J. S., Seeger R., and Pople J. A. 1980, J. Chem. Phys. 72, 650-654.
  • McLean A. D. and Chandler G. S., 1980, .J. Chem. Phys. 72, 5639.
  • Becke A. D., Phys. Rev. A 1988, 38, 3098–3100.
  • Lee C., Yang W., and Parr R. G., Phys. Rev. B 1988, 37, 785.
  • Vosko S. H., Wilk L., and Nusair M., 1980, Can. J. Phys. 58, 1200-1211.
  • Kuş, N., Breda, S., Reva, I., Tasal, E., Ogretir, C., and Fausto, R. 2007, Photochem. Photobiol., 83, 1237-1253. Erratum: ibidim, 83, 1541.
  • Kuş, N., Breda, S., and Fausto, R. 2009, J. Mol. Struct., 81, 924-926.
  • Reva, I.D., Nowak, M.J., Lapinski, L., and Fausto, R. 2008, Chem. Phys. Lett., 452, 20-28.
  • Kuş, N., Reva, I., and Fausto, R. 2010, J. Phys. Chem. A., 114, 7716–7724.

Year 2018, Volume 5, Issue 2, 55 - 63, 28.12.2018

Abstract

References

  • Whittle, E., Dows, D.A., and Pimentel, G.C. 1954, J. Chem. Phys., 22, 1943-1944.
  • Norman, I., and Porter, G. 1954, Nature, 174, 508-509.
  • Lin, C.Y., and Krantz, A. 1972, J. Chem. Soc. Chem. Commun., 19, 1111/1112, 1316.
  • Chapman, O.L., McIntosh, C.L., and Pacansky, J. 1973, J. Am. Chem. Soc., 95, 244-246.
  • Pong, R.G.S., and Shirk, J.S. 1973, J. Am. Chem. Soc., 95, 248-249.
  • Breda, S., Reva, I., Lapinski, L., and Fausto, R. 2004, Phys. Chem. Chem. Phys., 6, 929-937.
  • Rochkind, M.M. 1967, Anal. Chem., 39, 567-574.
  • Perutz, R.N., and Turner, J.J. 1973, J. Chem. Soc., Faraday Trans. 2, 69, 452-461.
  • Barnes, A.J., Bignall, J.C., and Purnell, C.J. 1975, J. Raman Spectrosc., 4, 159.
  • Lapinski, L., Rostkowska, H., Khvorostov, A., Fausto, R., and Nowak, M.J. 2003, J. Phys. Chem. A, 107, 5913-5919.
  • Szczesniak, M., Leszczynski, J., and Person, W.B. 1992, J. Am. Chem. Soc., 114, 2731-2733.
  • Buyl, F., Smets, J., Maes, G., and Adamowicz, L. 1995, J. Phys. Chem., 99, 14967-14979.
  • Stepanian, S.G., Reva, I.D., Radchenko, E.D., Rosado, M.T.S., Duarte, M.L.T.S., Fausto, R., and Adamowicz, L. 1998, J. Phys. Chem., 102, 1041–1054.
  • Jarmelo, S., Lapinski, L., Nowak, M.J., Carey, P.R., and Fausto, R. 2005, J. Phys. Chem. A, 109, 5689.
  • Gómez-Zavaglia, A., Reva, I.D., and Fausto, R. 2003, Phys. Chem. Chem. Phys., 5, 41-51.
  • Gómez-Zavaglia, A., and Fausto, R. 2003, Vibrat. Spectrosc., 33, 105-126.
  • Stepanian, S.G., Reva, I.D., Radchenko, E.D. and Adamowicz, L. 1998, J. Phys. Chem. A, 102, 4623-4629.
  • Kaczor, A., Reva, I.D., Proniewicz, L.M., and Fausto, R. 2006, J. Phys. Chem. A, 110, 2360-2370.
  • See, for example, (a) Reva, I.D., Jarmelo, S., Lapinski, L., and Fausto, R., 2004, Chem. Phys. Lett., 389, 68. (b) Ramaekers, R., Maes, G., Adamowicz, L., and Dkhissi, A. 2001, J. Mol. Struct., 560, 205. (c) Borba, A., Gómez-Zavaglia, A., Lapinski, L., and Fausto, R. 2004, Phys. Chem. Chem. Phys., 6, 2101. (d) Sander, W., Wandel, H., Bucher, G., Grafenstein, J., Kraka, E., and Cremer, D. 1998, J. Am. Chem. Soc., 120, 8480.
  • Chapman, O.L., McIntosh, C.L., and Pacansky, J. 1973, J. Am. Chem. Soc., 95, 614-617.
  • M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, J.E. Peralta Jr, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision A.0.2, Gaussian, Inc., Wallingford CT, 2009.
  • Raghavachari K., Binkley J. S., Seeger R., and Pople J. A. 1980, J. Chem. Phys. 72, 650-654.
  • McLean A. D. and Chandler G. S., 1980, .J. Chem. Phys. 72, 5639.
  • Becke A. D., Phys. Rev. A 1988, 38, 3098–3100.
  • Lee C., Yang W., and Parr R. G., Phys. Rev. B 1988, 37, 785.
  • Vosko S. H., Wilk L., and Nusair M., 1980, Can. J. Phys. 58, 1200-1211.
  • Kuş, N., Breda, S., Reva, I., Tasal, E., Ogretir, C., and Fausto, R. 2007, Photochem. Photobiol., 83, 1237-1253. Erratum: ibidim, 83, 1541.
  • Kuş, N., Breda, S., and Fausto, R. 2009, J. Mol. Struct., 81, 924-926.
  • Reva, I.D., Nowak, M.J., Lapinski, L., and Fausto, R. 2008, Chem. Phys. Lett., 452, 20-28.
  • Kuş, N., Reva, I., and Fausto, R. 2010, J. Phys. Chem. A., 114, 7716–7724.

Details

Primary Language English
Journal Section Articles
Authors

Nihal KUŞ> (Primary Author)
FEN FAKÜLTESİ
0000-0003-4162-7152
Türkiye

Publication Date December 28, 2018
Application Date September 26, 2018
Acceptance Date November 13, 2018
Published in Issue Year 2018, Volume 5, Issue 2

Cite

APA Kuş, N. (2018). Photo-Isomerization and Decarboxilation of 2-Amino-5-Chlorobenzoic Acid in Argon Matrix . Bilecik Şeyh Edebali Üniversitesi Fen Bilimleri Dergisi , 5 (2) , 55-63 . Retrieved from https://dergipark.org.tr/en/pub/bseufbd/issue/41708/464098