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

Yıl 2018, Cilt: 5 Sayı: 2, 55 - 63, 28.12.2018

Öz

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.

Kaynakça

  • 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.
Yıl 2018, Cilt: 5 Sayı: 2, 55 - 63, 28.12.2018

Öz

Kaynakça

  • 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.
Toplam 30 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Makaleler
Yazarlar

Nihal Kuş

Yayımlanma Tarihi 28 Aralık 2018
Gönderilme Tarihi 26 Eylül 2018
Kabul Tarihi 13 Kasım 2018
Yayımlandığı Sayı Yıl 2018 Cilt: 5 Sayı: 2

Kaynak Göster

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.