Investigation on intramolecular hydrogen bond and some thermodynamic properties of polyhydroxylated anthraquinones

Journal of Chemical and Engineering Data

Volumn 57, Issue 9, 2012, Pages 2442-2455

  Qu, Ruijuan ^a   Liu, Hongxia ^b   Feng, Mingbao ^a   Yang, Xi ^a   Wang, Zunyao ^a  

^a NANJING UNIVERSITY   (China)

^b JIAXING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS IN MOLECULES; FIRST-ORDER IONIZATION; GAUSSIANS; HYDROXYL SUBSTITUTION; INTRAMOLECULAR HYDROGEN BOND; ISODESMIC REACTIONS; SELF-CONSISTENT REACTION FIELDS; STANDARD ENTHALPY OF FORMATION; STANDARD GIBBS ENERGY;

HYDROXYLATION; IONIZATION; ISOMERS; KETONES;

HYDROGEN BONDS;

EID: 84866428440     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je300407g     Document Type: Article

References (43)

1. Thomson, R. H. Naturally occurring quinones; Academic Press: New York, 1967.
2. Routier, S.; Bernier, J. L.; Catteau, J. P.; Riou, J. F.; Bailly, C. Synthesis, DNA binding, topoisomerase II inhibition and cytotoxicity of two guanidine-containing anthracene-9,10-diones Anti-Cancer Drug Des. 1998, 13, 407-415
3. Das, S.; Saha, A.; Mandal, P. C. Studies on the formation of Cu(II) and Ni(II) complexes of 1,2-dihydroxy-9,10-anthraquinone and lack of stimulated superoxide formation by the complexes Talanta 1996, 43, 95-102
4. Liu, H. T.; Han, P.; Wen, Y. Y.; Luan, F.; Gao, Y.; Li, X. Y. Quantitative structure-electrochemistry relationship for variously-substituted 9, 10-anthraquinones using both an heuristic method and a radial basis function neural network Dyes Pigm. 2010, 84, 148-152
5. Shi, Y. Q.; Fukai, T.; Sakagami, H.; Kuroda, J.; Miyaoka, R.; Tamura, M.; Yoshida, N.; Nomura, T. Cytotoxic and DNA damage-inducing activities of low molecular weight phenols from rhubarb Anticancer Res. 2001, 21, 2847-2853
6. Muzychkina, R. A.; Tolstikov, G. A. Natural anthraquinone: biological properties and physicochemical characteristics; Phasis: Moscow, 1998.
7. Fain, V. Y. 9,10-Anthraquinones and their application; Photochemistry Center: Moscow, 1999.
8. Kotting, C.; Sander, W.; Breidung, J.; Thiel, W.; Senzlober, M.; Burger, H. A charge-transfer complex of xenon and difluorovinylidene J. Am. Chem. Soc. 1998, 120, 219-220
9. Lown, J. W. Discovery and development of anthracycline antitumour antibiotics Chem. Soc. Rev. 1993, 22, 165-176
10. Nicolau, K. C.; Dai, W. M.; Hong, Y. P.; Baldridge, K. K.; Siegel, J. S.; Tsay, S. C. Molecular design, chemical synthesis, kinetic studies, calculations, and biological studies of novel enediynes equipped with triggering, detection, and deactivating devices. Model dynemicin A epoxide and cis-diol systems J. Am. Chem. Soc. 1993, 115, 7944-7953
11. Frackowiak, A.; Skibinski, P.; Gawel, W.; Zaczynska, E.; Czarny, A.; Gancarz, R. Synthesis of glycoside derivatives of hydroxyanthraquinone with ability to dissolve and inhibit formation of crystals of calcium oxalate. Potential compounds in kidney stone therapy Eur. J. Med. Chem. 2010, 45, 1001-1007
12. Tabaraki, R.; Khayamian, T.; Ensafi, A. A. Wavelet neural network modeling in QSPR for prediction of solubility of 25 anthraquinone dyes at different temperatures and pressures in supercritical carbon dioxide J. Mol. Graph. Modell. 2006, 25, 46-54
13. Comini, L. R.; Núñez Montoya, S. C.; Sarmiento, M.; Cabrera, J. L.; Arguello Gustavo, A. Characterizing some photophysical, photochemical and photobiological properties of photosensitizing anthraquinones J. Photochem. Photobiol., A: Chem. 2007, 188, 185-191
14. Khan, A. T.; Blessing, B.; Schmidt, R. R. An expedient and efficient synthesis of naturally occurring hydroxy substituted anthraquinones Synthesis 1994, 3, 255-257
15. Fain, V. Y.; Zaitsev, B. E.; Ryabov, M. A. Anthraquinones tautomerism: VII. Hydroxy-substituted anthraquinones Russ. J. Org. Chem. 2007, 43 (10) 1460-1465
16. +) Thermochim. Acta 2002, 388, 227-232
17. 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 Thermochim. Acta 2005, 436 (1-2) 56-67
18. Hao, Y.; Peng, J.; Hu, S. W.; Li, J. Q.; Zhai, M. L. Thermal decomposition of allyl-imidazolium-based ionic liquid studied by TGA-MS analysis and DFT calculations Thermochim. Acta 2010, 501, 78-83
19. Wang, C.; Liu, H. X.; Fang, Z. Y.; Wang, Z. Y. DFT calculation on polychlorinated anthraquinones: their gas phase thermodynamic function and implication of Cl substituted position J. Chem. Eng. Data 2010, 55, 1077-1086
20. Wang, H. D.; Liu, H.; Li, C. C; Wang, Z. Y.; Yang, G. Y. DFT calculation on PBPXs: Their gas phase thermodynamic function and implication of Br substituted position Thermochim. Acta 2009, 487, 49-53
21. Sun, P.; Yang, G. Y.; Liu, H. X.; Wang, Z. Y. DFT calculation on 76 polybromophenazines: their thermodynamic function and stability J. Chem. Eng. Data 2009, 54, 2404-2410
22. Yu, J.; Zhang, X. C.; Wang, Z. Y.; Zeng, X. L. Study on the Thermodynamic Properties and Stability of Series of Polybrominated Dibenzo-furans by Density Functional Theory Acta Chim. Sin. 2006, 64, 1961-1968
23. Schuster, P.; Zundel, G. The Hydrogen Bond, Recent Development in Theory and Experiment; North-Holland: Amsterdam, 1976.
24. Jablonski, M.; Kaczmarek, A.; Sadlej, A. J. Estimates of the energy of intramolecular hydrogen bonds J. Phys. Chem. A 2006, 110, 10890-10898
25. Nowroozi, A.; Raissi, H.; Farzad, F. The presentation of an approach for estimating the intramolecular hydrogen bond strength in conformational study of β-Aminoacrolein J. Mol. Struct.: THEOCHEM 2005, 730, 161-169
26. Woodford, J. N. Density Functional Theory and Atoms-in-Molecules Investigation of Intramolecular Hydrogen Bonding in Derivatives of Malonaldehyde and Implications for Resonance-Assisted Hydrogen Bonding J. Phys. Chem. A 2007, 111, 8519-8530
27. Biegler-Konig, F.; Schonbohm, J.; Bayles, D. AIM2000-a program to analyze and visualize atoms in molecules J. Comput. Chem. 2001, 22 (5) 545-559
28. Dean, J. A., Eds. Lange's Handbook of Chemistry, 13 th ed.; McGraw-Hill: New York, 1991.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E., Jr.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; 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.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. GAUSSIAN 09 (Revision A.02); Gaussian, Inc.: Wallingford CT, 2009.
30. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions J Phys. Chem. B 2009, 113, 6378-6396
31. a Using the Cluster-Continuum Model J. Phys. Chem. A 2002, 106, 7434-7439
32. Rozas, I.; Alkorta, I.; Elguero, J. Intramolecular Hydrogen Bonds in ortho-Substituted Hydroxybenzenes and in 8-Susbtituted 1-Hydroxynaphthalenes: Can a Methyl Group Be an Acceptor of Hydrogen Bonds Phys. Chem. A 2001, 105, 10462-10467
33. Bader, R. F. W. Atom In Molecules-A Quantum Theory; Oxford University Press: Oxford, 1990.
34. Bader, R. F. W. A quantum theory of molecular structure Chem. Rev. 1991, 91, 893-928
35. Popelier, P. L. A. Characterization of a dihydrogen bond on the basis of the electron density J. Phys. Chem. A 1998, 102, 1873-1878
36. Espinosa, E.; Lecomte, C.; Molins, E. Experimental electron density overlapping in hydrogen bonds: topology vs. energetics Chem. Phys. Lett. 1999, 300, 745-748
37. Espinosa, E.; Alkorta, I.; Rozas, I.; Elguero, J.; Molins, E. About the evaluation of the local kinetic, potential and total energy densities in closed-shell interactions Chem. Phys. Lett. 2001, 336 (5-6) 457-461
38. Abramov, Y. A. On the possibility of kinetic energy density evaluation from the experimental electron-density distribution Acta Crystallogr., A 1997, 53, 264-272
39. Espinosa, E.; Molins, E.; Lecomte, C. Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities Chem. Phys. Lett. 1998, 285 (3-4) 170-173
40. Parra, R. D.; Streu, K. Hydrogen bond cooperativity in polyols: A DFT and AIM study Comp. Theor. Chem. 2011, 967, 12-18
41. Parra, R. D.; Ohlssen, J. Cooperativity in intramolecular bifurcated hydrogen bonds: an ab initio study J. Phys. Chem. A 2008, 112, 3492-3498
42. Parra, R. D.; Streu, K. Cooperative effects in regular and bifurcated intramolecular OH⋯O=C interactions: A computational study Comp. Theor. Chem. 2011, 977, 181-187
43. SPSS 12.0 for Windows program; SPSS Inc.: Chicago, IL, 2003.