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DFT Thermochemical Investigation of Rearrangement for 3-Hydroxy Analogs of 2,3-Dihydrobenzothiophen-2- and -3-ones

Yıl 2007, Cilt: 35 Sayı: 3, 187 - 193, 01.08.2007

Deniz Hür

Öz

Thermodynamic and kinetic controlled reaction coordinate for the rearrangement of 2-benzotriazol-1-yl-2-alkyl-3phenyl-2,3-dihydro-benzo[b]thiophen-3-ol derivatives have been predicted by using DFT calculated thermodynamicproperties and comparing DFT calculated NMR and IR spectroscopic properties with experimental ones

Anahtar Kelimeler

DFT thermodynamic kinetic control benzotriazole

Kaynakça

  • 1. Tamura Y., Bayomi, S. M., Mukai, C., Ikeda, M.Murase, M., Kise, M. Sulfilimines in organic syntheses: new entries into tetrahydro-1,2- benzothiazepine and 1,2-benzisothiazole systems. Tetrahedron Lett. 21, 533,1980. (b) Tamura, Y., Bayomi, S. M., Mukai, C., Ikeda, M., Kise, M. Novel Conversion of Benzo[b]thiophen-3(2H)-ones into 1,2-Benzisothiazole and Tetrahydro-1,2- benzothiazepin-5-one Systems via Sulphimide Intermediates. J. Chem. Soc., Perkin Trans. 1 (1980) 2830.
  • 2. Beck, J. R. Facile Synthesis of 2-Phenyl benzo[b]thiophene-3-amin and corresponding Soxides. J. Heterocycl. Chem. 15 (1978) 513 .
  • 3. Cabiddu, M. G., Cabiddu, S., Fattuoni, C., Floris, C., Gelli, G., Melis, S. Metalation Reactions.19. Onestep Synthesis of 5-Membered HeterocyclicCompounds Involving The Dilithiated Species 2- Lithio [(1-Lithio-1-Methyl ethyl) sulfonyl] benzene. Synthesis, 41(1993).
  • 4. Regitz, M. Reaktionen Aktiver Methylen verbindungen mit aziden. V. Uber ein alpha-DiazoBeta-Keto-Sulfon. Chem. Ber. 98 (1965) 36 .
  • 5. Shenoy, V.U., Patel, V. P., Seshadri, S. Disperse Dyes Derived From 3-Oxo-2,3-Dihydrobenzo[b] Thiophene-1,1-dioxide and 3-Dicyanomethylene2,3-dihydrobenzo [b] thiophene-1,1-dioxide. Dyes and Pigments, 11 (1989) 37.
  • 6. (a) Hudson, A. T., Pether, M. J. Formation of 2-Acyl benzo [b] thiophen- 3 -(2H) -ones from 2- Substitued 3-Chlorothichromen-4-ones. J.Chem. Res. (S), 56 1983. (b) Gabbutt, C. D., Hepworth, J. D., Heron, B. M., Kanjia, M. Ring contraction of sulfenamides derived from thiochroman-4-ones. Tetrahedron, 50 (1994) 827.
  • 7. Katritzky, A. R., Kirichenko, K., Hür, D., Zhao, X., Ji, Y, Steel, P.J. Synthesis of 2,3-dihydrobenzofuran-2- ones and 2,3-dihydrobenzothiophene-2- and 3-ones by rearrangements of 3-hydroxy analogs. ARKIVOC, vi, 27 (2004).
  • 8. Hamdach, A., El Hadrami, E. M., Hajji, C., ZaballosGarcia, E., Sepulveda-Arques, J., Zaragoza, R. J. Experimental and theoretical DFT study of the reaction of 3-amino-1,2-diols with dichloromethane and paraformaldehyde. Tetrahedron, 60 (2004) 10353.
  • 9. Hermida-Ramon, J.M., Pena-Gallego, A., MartinezNunez, E., Fernandez-Ramos, A., Cabaleiro-Lago, E. M. A quantum chemical study of aniline/ammonia clusters. Thermodynamic pro-perties and frequency analysis. Journal of Molecular Structure (Theochem), 497 (2000) 105, .
  • 10. Bazyleva, A. B., Kabo, G. J., Paulechka, Y. U., Zaitsau, D. H., Blokhin, A.V., Sevruk, V. M. The thermodynamic properties of 1-bromoadamantane in the gaseous state. Thermochimica Acta, 436 (2005) 56 .
  • 11. Parker, J. K., Nelson, H. H. Kinetics and thermodynamics of the Al + trimethylaluminum reaction. Chemical Physics Letters, 360, 313, 2002.
  • 12. Cordfunke, E. H. P., Groen, C. P. A thermodynamic study of gaseous BaSiO3. J. Chem. Thermodynamics, 32 (2000) 839.
  • 13. Wandschneider, D., Michalik, M., Heintz, A. Spectroscopic and thermodynamic studies of liquid n-butanol + n-hexane and + cyclohexane mixtures based on quantum mechanical ab initio calculations of n-butanol clusters. Journal of Molecular Liquids, 125 (2006) 2 .
  • 14. Wang, Z., Zhai, Z., Wang, L., Chen, J., Kikuchi, O., Watanabe, T. Prediction of gas phase thermodynamic function of polychlorinated dibenzo -p-dioxins using DFT. J. Molecular Structure (Theochem), 672 (2004) 97 .
  • 15. Katritzky, A. R., Xie, L., Serdyuk, L. Novel and Efficient Insertions of Carbons Carrying O-, S-, and N-Linked Substituents: Synthesis of -Alkoxyalkyl, - (Alkylthio)alkyl, and -(Carbazol-9-yl)alkyl Ketones. J. Org. Chem., 61(1996) 7564, .
  • 16. Gaussian 03, Revision C.02, Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, Jr., J. A., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., and Pople, J. A., Gaussian, Inc., Wallingford CT, 2004.
  • 17. (a) Becke, A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648. (b) Lee, C., Yang, W., Parr, R. G. Development of the Colle-Salvetti correlationenergy formula into a functional of the electron density. Phys. Rev. B, 37 (1988) 785 .
  • 18. (a) Muller, C., Plesset, M. S., Note on an Approximation Treatment for Many-Electron Systems. Phys. Rev., 46, 618, 1934. (b) Bartlett, R. J., Silver, D. M. Many-body perturbation theory applied to electron pair correlation energies. I. Closed-shell first-row diatomic hydrides. J. Chem.Phys., 62, 3258, 1975. (c) Lee, C., Yang, W., Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B, 37, 785, 1988. (e) Becke, A. D. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A , 38 (1988) 3098 .
  • 19. Onsager, L. Electric Moments of Molecules in Liquids. J. Am. Chem. Soc., 58 (1936) 1486 .
  • 20. Foresman, J. B., Keith, T. A., Wiberg, K. B., Snoonian, J., Frisch, M. J. Solvent Effects. 5. Influence of Cavity Shape, Truncation of Electrostatics, and Electron Correlation on ab Initio Reaction Field Calculations. J. Phys. Chem., 100 (1996) 16098.
  • 21. Foresman, J. B., Frisch, Æ. Exploring Chemistry with Electronic Structure Methods. Gaussian Inc., Pittsburgh, PA, (1996).

Yıl 2007, Cilt: 35 Sayı: 3, 187 - 193, 01.08.2007

Deniz Hür

Öz

Kaynakça

  • 1. Tamura Y., Bayomi, S. M., Mukai, C., Ikeda, M.Murase, M., Kise, M. Sulfilimines in organic syntheses: new entries into tetrahydro-1,2- benzothiazepine and 1,2-benzisothiazole systems. Tetrahedron Lett. 21, 533,1980. (b) Tamura, Y., Bayomi, S. M., Mukai, C., Ikeda, M., Kise, M. Novel Conversion of Benzo[b]thiophen-3(2H)-ones into 1,2-Benzisothiazole and Tetrahydro-1,2- benzothiazepin-5-one Systems via Sulphimide Intermediates. J. Chem. Soc., Perkin Trans. 1 (1980) 2830.
  • 2. Beck, J. R. Facile Synthesis of 2-Phenyl benzo[b]thiophene-3-amin and corresponding Soxides. J. Heterocycl. Chem. 15 (1978) 513 .
  • 3. Cabiddu, M. G., Cabiddu, S., Fattuoni, C., Floris, C., Gelli, G., Melis, S. Metalation Reactions.19. Onestep Synthesis of 5-Membered HeterocyclicCompounds Involving The Dilithiated Species 2- Lithio [(1-Lithio-1-Methyl ethyl) sulfonyl] benzene. Synthesis, 41(1993).
  • 4. Regitz, M. Reaktionen Aktiver Methylen verbindungen mit aziden. V. Uber ein alpha-DiazoBeta-Keto-Sulfon. Chem. Ber. 98 (1965) 36 .
  • 5. Shenoy, V.U., Patel, V. P., Seshadri, S. Disperse Dyes Derived From 3-Oxo-2,3-Dihydrobenzo[b] Thiophene-1,1-dioxide and 3-Dicyanomethylene2,3-dihydrobenzo [b] thiophene-1,1-dioxide. Dyes and Pigments, 11 (1989) 37.
  • 6. (a) Hudson, A. T., Pether, M. J. Formation of 2-Acyl benzo [b] thiophen- 3 -(2H) -ones from 2- Substitued 3-Chlorothichromen-4-ones. J.Chem. Res. (S), 56 1983. (b) Gabbutt, C. D., Hepworth, J. D., Heron, B. M., Kanjia, M. Ring contraction of sulfenamides derived from thiochroman-4-ones. Tetrahedron, 50 (1994) 827.
  • 7. Katritzky, A. R., Kirichenko, K., Hür, D., Zhao, X., Ji, Y, Steel, P.J. Synthesis of 2,3-dihydrobenzofuran-2- ones and 2,3-dihydrobenzothiophene-2- and 3-ones by rearrangements of 3-hydroxy analogs. ARKIVOC, vi, 27 (2004).
  • 8. Hamdach, A., El Hadrami, E. M., Hajji, C., ZaballosGarcia, E., Sepulveda-Arques, J., Zaragoza, R. J. Experimental and theoretical DFT study of the reaction of 3-amino-1,2-diols with dichloromethane and paraformaldehyde. Tetrahedron, 60 (2004) 10353.
  • 9. Hermida-Ramon, J.M., Pena-Gallego, A., MartinezNunez, E., Fernandez-Ramos, A., Cabaleiro-Lago, E. M. A quantum chemical study of aniline/ammonia clusters. Thermodynamic pro-perties and frequency analysis. Journal of Molecular Structure (Theochem), 497 (2000) 105, .
  • 10. Bazyleva, A. B., Kabo, G. J., Paulechka, Y. U., Zaitsau, D. H., Blokhin, A.V., Sevruk, V. M. The thermodynamic properties of 1-bromoadamantane in the gaseous state. Thermochimica Acta, 436 (2005) 56 .
  • 11. Parker, J. K., Nelson, H. H. Kinetics and thermodynamics of the Al + trimethylaluminum reaction. Chemical Physics Letters, 360, 313, 2002.
  • 12. Cordfunke, E. H. P., Groen, C. P. A thermodynamic study of gaseous BaSiO3. J. Chem. Thermodynamics, 32 (2000) 839.
  • 13. Wandschneider, D., Michalik, M., Heintz, A. Spectroscopic and thermodynamic studies of liquid n-butanol + n-hexane and + cyclohexane mixtures based on quantum mechanical ab initio calculations of n-butanol clusters. Journal of Molecular Liquids, 125 (2006) 2 .
  • 14. Wang, Z., Zhai, Z., Wang, L., Chen, J., Kikuchi, O., Watanabe, T. Prediction of gas phase thermodynamic function of polychlorinated dibenzo -p-dioxins using DFT. J. Molecular Structure (Theochem), 672 (2004) 97 .
  • 15. Katritzky, A. R., Xie, L., Serdyuk, L. Novel and Efficient Insertions of Carbons Carrying O-, S-, and N-Linked Substituents: Synthesis of -Alkoxyalkyl, - (Alkylthio)alkyl, and -(Carbazol-9-yl)alkyl Ketones. J. Org. Chem., 61(1996) 7564, .
  • 16. Gaussian 03, Revision C.02, Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, Jr., J. A., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., and Pople, J. A., Gaussian, Inc., Wallingford CT, 2004.
  • 17. (a) Becke, A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648. (b) Lee, C., Yang, W., Parr, R. G. Development of the Colle-Salvetti correlationenergy formula into a functional of the electron density. Phys. Rev. B, 37 (1988) 785 .
  • 18. (a) Muller, C., Plesset, M. S., Note on an Approximation Treatment for Many-Electron Systems. Phys. Rev., 46, 618, 1934. (b) Bartlett, R. J., Silver, D. M. Many-body perturbation theory applied to electron pair correlation energies. I. Closed-shell first-row diatomic hydrides. J. Chem.Phys., 62, 3258, 1975. (c) Lee, C., Yang, W., Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B, 37, 785, 1988. (e) Becke, A. D. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A , 38 (1988) 3098 .
  • 19. Onsager, L. Electric Moments of Molecules in Liquids. J. Am. Chem. Soc., 58 (1936) 1486 .
  • 20. Foresman, J. B., Keith, T. A., Wiberg, K. B., Snoonian, J., Frisch, M. J. Solvent Effects. 5. Influence of Cavity Shape, Truncation of Electrostatics, and Electron Correlation on ab Initio Reaction Field Calculations. J. Phys. Chem., 100 (1996) 16098.
  • 21. Foresman, J. B., Frisch, Æ. Exploring Chemistry with Electronic Structure Methods. Gaussian Inc., Pittsburgh, PA, (1996).
Toplam 21 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Research Article
Yazarlar

Deniz Hür Bu kişi benim

Yayımlanma Tarihi 1 Ağustos 2007
Yayımlandığı Sayı Yıl 2007 Cilt: 35 Sayı: 3

Kaynak Göster

APA Hür, D. (2007). DFT Thermochemical Investigation of Rearrangement for 3-Hydroxy Analogs of 2,3-Dihydrobenzothiophen-2- and -3-ones. Hacettepe Journal of Biology and Chemistry, 35(3), 187-193.
AMA Hür D. DFT Thermochemical Investigation of Rearrangement for 3-Hydroxy Analogs of 2,3-Dihydrobenzothiophen-2- and -3-ones. HJBC. Ağustos 2007;35(3):187-193.
Chicago Hür, Deniz. “DFT Thermochemical Investigation of Rearrangement for 3-Hydroxy Analogs of 2,3-Dihydrobenzothiophen-2- and -3-Ones”. Hacettepe Journal of Biology and Chemistry 35, sy. 3 (Ağustos 2007): 187-93.
EndNote Hür D (01 Ağustos 2007) DFT Thermochemical Investigation of Rearrangement for 3-Hydroxy Analogs of 2,3-Dihydrobenzothiophen-2- and -3-ones. Hacettepe Journal of Biology and Chemistry 35 3 187–193.
IEEE D. Hür, “DFT Thermochemical Investigation of Rearrangement for 3-Hydroxy Analogs of 2,3-Dihydrobenzothiophen-2- and -3-ones”, HJBC, c. 35, sy. 3, ss. 187–193, 2007.
ISNAD Hür, Deniz. “DFT Thermochemical Investigation of Rearrangement for 3-Hydroxy Analogs of 2,3-Dihydrobenzothiophen-2- and -3-Ones”. Hacettepe Journal of Biology and Chemistry 35/3 (Ağustos 2007), 187-193.
JAMA Hür D. DFT Thermochemical Investigation of Rearrangement for 3-Hydroxy Analogs of 2,3-Dihydrobenzothiophen-2- and -3-ones. HJBC. 2007;35:187–193.
MLA Hür, Deniz. “DFT Thermochemical Investigation of Rearrangement for 3-Hydroxy Analogs of 2,3-Dihydrobenzothiophen-2- and -3-Ones”. Hacettepe Journal of Biology and Chemistry, c. 35, sy. 3, 2007, ss. 187-93.
Vancouver Hür D. DFT Thermochemical Investigation of Rearrangement for 3-Hydroxy Analogs of 2,3-Dihydrobenzothiophen-2- and -3-ones. HJBC. 2007;35(3):187-93.

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