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Reactivity and structure of derivatives of 2-hydroxy-1,4-naphthoquinone (lawsone) 원문보기

Journal of physical organic chemistry, v.21 no.12, 2008년, pp.1022 - 1028  

Lamoureux, G. (Escuela de Quí) ,  Perez, Alice L. (mica and Centro de Investigaciones en Productos Naturales, Universidad de Costa Rica, 2060 San Pedro, San José) ,  Araya, Mario (, Costa Rica) ,  Agüero, Christian (Escuela de Quí)

Abstract AI-Helper 아이콘AI-Helper

The structures of two derivatives of 2-hydroxy-1,4-naphthoquinone (lawsone) are examined using the density functional theory (DFT) hybrid functional B3LYP. Using the optimized structure of lawsone acetate, the reactivity of acyl transfer is described. Also, the nucleophilicity of the conjugate base ...

주제어

참고문헌 (41)

  1. Naturally Occurring Quinones Thomson R. H 1971 

  2. Kutyrev, A.A.. Nucleophilic reactions of quinones. Tetrahedron, vol.47, no.38, 8043-8065.

  3. Rozeboom, Melvin D., Tegmo-Larsson, Inga Mai, Houk, K. N.. Frontier molecular orbital theory of substitutent effects on regioselectivities of nucleophilic additions and cycloadditions to benzoquinones and naphthoquinones. Journal of organic chemistry, vol.46, no.11, 2338-2345.

  4. Afzal, Muhammad, Al-Oriquat, Galib, M. Al-Hassan, Jassim, Muhammad, Nazar. Isolation of 1,2-Dihydroxy-4-glucosyloxynaphthalene from Lawsonia Innermis. Heterocycles, vol.22, no.4, 813-.

  5. Acta Cryst. Dekkers J. 2896 52 1996 

  6. Khan, Mohd. Shahid, Khan, Zahid H.. Ab initio and semiempirical study of structure and electronic spectra of hydroxy substituted naphthoquinones. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, vol.61, no.4, 777-790.

  7. Rostkowska, Hanna, Nowak, Maciej J., Lapinski, Leszek, Adamowicz, Ludwik. Molecular structure and infrared spectra of 2-hydroxy-1,4- naphthoquinone; Experimental matrix isolation and theoretical Hartree–Fock and post Hartree–Fock study. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, vol.54, no.8, 1091-1103.

  8. Idriss, K. A., Sedaira, H., Hashem, E. Y., Saleh, M. S., Soliman, S. A.. The visible absorbance maximum of 2-hydroxy-1,4-naphthoquinone as a novel probe for the hydrogen bond donor abilities of solvents and solvent mixtures. Monatshefte für Chemie = Chemical monthly, vol.127, no.1, 29-42.

  9. Padhye, S. B., Kulkarni, B. A.. Hydrogen bonding interaction of some naturally occurring isomeric juglones with dioxane. The Journal of physical chemistry, vol.79, no.9, 927-928.

  10. Becke, A. D.. Density-functional exchange-energy approximation with correct asymptotic behavior. Physical review. A, General physics, vol.38, no.6, 3098-3100.

  11. Becke, Axel D.. Density-functional thermochemistry. III. The role of exact exchange. The Journal of chemical physics, vol.98, no.7, 5648-5652.

  12. Lee, Chengteh, Yang, Weitao, Parr, Robert G.. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical review. B, Condensed matter, vol.37, no.2, 785-789.

  13. Katritzky, Alan R., Suzuki, Kazuyuki, Singh, Sandeep K.. N-Acylation in combinatorial chemistry. ARKIVOC : Archive for organic chemistry, vol.2004, no.1, 12-35.

  14. Fieser, Louis F., Berliner, Ernst, Bondhus, Frances J., Chang, Frederic C., Dauben, William G., Ettlinger, Martin G., Fawaz, George, Fields, Melvin, Fieser, Mary, Heidelberger, Charles, Heymann, Hans, Seligman, Arnold M., Vaughan, Wyman R., Wilson, Armin G., Wilson, Evelyn, Wu, Mao-i, Leffler, Marlin T., Hamlin, K. E., Hathaway, Robert J., Matson, Edward J., Moore, E. E., Moore, M. B., Rapala, Richard T., Zaugg, Harold E.. Naphthoquinone Antimalarials. I. General Survey1,2. Journal of the American Chemical Society, vol.70, no.10, 3151-3155.

  15. Krishnamurthy, Subrahmanya. The principle of vinylogy. Journal of chemical education, vol.59, no.7, 543-.

  16. Schmidt, Michael W., Baldridge, Kim K., Boatz, Jerry A., Elbert, Steven T., Gordon, Mark S., Jensen, Jan H., Koseki, Shiro, Matsunaga, Nikita, Nguyen, Kiet A., Su, Shujun, Windus, Theresa L., Dupuis, Michel, Montgomery Jr, John A.. General atomic and molecular electronic structure system. Journal of computational chemistry, vol.14, no.11, 1347-1363.

  17. Bode, B.M., Gordon, M.S.. Macmolplt: a graphical user interface for GAMESS. Journal of molecular graphics & modelling, vol.16, no.3, 133-138.

  18. Wu, G., Shlykov, S., Van Alsenoy, C., Geise, H. J., Sluyts, E., Van der Veken, B. J.. Formic Acetic Anhydride in the Gas Phase, Studied by Electron Diffraction and Infrared Spectroscopy, Supplemented with ab-Initio Calculations of Geometries and Force Fields. The Journal of physical chemistry, vol.100, no.28, 11620-11629.

  19. Yamada, S., Sugaki, T., Matsuzaki, K.. Twisted Amides as Selective Acylating Agents for Hydroxyl Groups under Neutral Conditions: Models for Activated Peptides during Enzymatic Acyl Transfer Reaction. Journal of organic chemistry, vol.61, no.17, 5932-5938.

  20. Buergi, Hans Beat, Dunitz, Jack D.. From crystal statics to chemical dynamics. Accounts of chemical research, vol.16, no.5, 153-161.

  21. M.Araya Thesis Universidad de Costa Rica (2007). 

  22. Stowasser, R., Hoffmann, R.. What Do the Kohn−Sham Orbitals and Eigenvalues Mean?. Journal of the American Chemical Society, vol.121, no.14, 3414-3420.

  23. Kongkathip, Ngampong, Kongkathip, Boonsong, Siripong, Pongpun, Sangma, Chak, Luangkamin, Suwaporn, Niyomdecha, Momad, Pattanapa, Suppachai, Piyaviriyagul, Suratsawadee, Kongsaeree, Palangpon. Potent antitumor activity of synthetic 1,2-Naphthoquinones and 1,4-Naphthoquinones. Bioorganic & medicinal chemistry, vol.11, no.14, 3179-3191.

  24. Ambident Anions, translation from Russian Reutov O. A. 1983 

  25. Le NOBLE, W. J.. Conditions for the Alkylation of Ambident Anions. Synthesis : journal of synthetic organic chemistry, vol.1970, no.1, 1-6.

  26. Hard and Soft Acids and Bases Pearson R. G. 1973 

  27. Pearson, Ralph G.. Hard and Soft Acids and Bases. Journal of the American Chemical Society, vol.85, no.22, 3533-3539.

  28. Elango, M., Parthasarathi, R., Subramanian, V., Chattaraj, P. K.. Alkylation of enolates: An electrophilicity perspective. International journal of quantum chemistry, vol.106, no.4, 852-862.

  29. Roy, R. K., Tajima, N., Hirao, K.. A Simple Model to Predict Preferable Aldol Products from Unsymmetrical Ketones Using Local Hard−Soft Acid−Base Concept. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory, vol.105, no.10, 2117-2124.

  30. Damoun, S., Van de Woude, G., Choho, K., Geerlings, P.. Influence of Alkylating Reagent Softness on the Regioselectivity in Enolate Ion Alkylation: A Theoretical Local Hard and Soft Acids and Bases Study. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory, vol.103, no.39, 7861-7866.

  31. Mendez, Francisco, Gazquez, Jose L.. Chemical Reactivity of Enolate Ions: The Local Hard and Soft Acids and Bases Principle Viewpoint. Journal of the American Chemical Society, vol.116, no.20, 9298-9301.

  32. Chattaraj, P. K., Sarkar, U., Roy, D. R.. Electrophilicity Index. Chemical reviews, vol.106, no.6, 2065-2091.

  33. Geerlings, P., De Proft, F., Langenaeker, W.. Conceptual Density Functional Theory. Chemical reviews, vol.103, no.5, 1793-1874.

  34. Computational Chemistry: Introduction to the Theory and Applications of Molecular and Quantum Mechanics Lewars E. 428 2004 

  35. Nguyen, L. T., Le, T. N., De Proft, F., Chandra, A. K., Langenaeker, W., Nguyen, M. T., Geerlings, P.. Mechanism of [2 + 1] Cycloadditions of Hydrogen Isocyanide to Alkynes: Molecular Orbital and Density Functional Theory Study. Journal of the American Chemical Society, vol.121, no.25, 5992-6001.

  36. Yang, Weitao., Mortier, Wilfried J.. The use of global and local molecular parameters for the analysis of the gas-phase basicity of amines. Journal of the American Chemical Society, vol.108, no.19, 5708-5711.

  37. Roy, R. K., Krishnamurti, S., Geerlings, P., Pal, S.. Local Softness and Hardness Based Reactivity Descriptors for Predicting Intra- and Intermolecular Reactivity Sequences: Carbonyl Compounds. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory, vol.102, no.21, 3746-3755.

  38. Roy, R. K., de Proft, F., Geerlings, P.. Site of Protonation in Aniline and Substituted Anilines in the Gas Phase: A Study via the Local Hard and Soft Acids and Bases Concept. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory, vol.102, no.35, 7035-7040.

  39. Adv. Chem. Phys. Lowdin P. O. 185 5 1970 

  40. Phys. Chem. Comm. Mondal P. 24 6 2003 

  41. Miertus̃, S.. Approximate evaluations of the electrostatic free energy and internal energy changes in solution processes. Chemical physics, vol.65, no.2, 239-245.

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