Crystal structures of aminophenalenones with relation to their spectral properties

Zeitschrift fur Kristallographie

Volumn 213, Issue 9, 1998, Pages 466-472

  Yatsenko, A V ^a   Tafeenko, V A ^a   Paseshnichenko, K A ^a   Stalnaya, T V ^b   Solodar, S L ^b  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b Organic Intermediates and Dyes Institute   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000217518     PISSN: 00442968     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

1. Orlov, V. D.; Solodar, S. L.; Surov, Yu. N.; Tsyguleva, O. M.; Vinogradov, L. M.: Reactions of polycyclic ketones. XXI. Electronic structure of phenalenone. Zh. Org. Khim. (Rus.) 17 (1981) 1964-1968.
2. Orlov, V. D.; Solodar, S. L.; Surov, Yu. N.; Vinogradov, L. M.; Chistova, S. E.: Reactions of polycyclic ketones. XXIII. IR Spectra, relative basicity and dipole moments of phenalenone derivatives. Zh. Org. Khim. (Rus.) 18 (1982) 615-620.
3. Kuznetsova, N. A.; Reznichenko, A. V.; Kokin, V. N.; Kaliya, O. L.: Photolysis of 6-substituted phenalenones in deaerated alcohol media. Zh. Org. Khim. (Rus.) 18 (1982) 620-624.
4. Efendiev, T. Sh.; Katarkevich, V. M.; Rubinov, A. N.: Generation of tunable picosecond pulses in a simple distributed feedback dye laser under nitrogen-laser pumping. Opt. Commun. 55 (1985) 347-352.
5. Ayyangar, N. R.; Joshi, S. V; Srinivasan, K. V.; Puranik, V. G.; Tavale, S. S.: Row, T. N. G.: Polycyclic compounds: part III -color and chemical constitution of 2-aryl phenalen-1-one derivatives. Dyes. Pigm. 7 (1986) 81-92.
6. Negrebetskii, V. V.: Multinuclear NMR study of proton-acceptor properties of substituted phenalenones. Zh. Obschch. Khim. (Rus.) 64 (1994) 831-836.
7. Carnovale, F.; Gan, T. H.; Peel, J. B.; Franz, K. D.: The photoelectron spectra of some 1,9-disubstituted phenalenes. J. Chem. Soc. Perkin Trans II (1980) 957-960.
8. Franz, K. D.: 1 ,9-Disubstituted phenalenes. 4. Preparation and properties of 1,9-diheterosubstituted phenalenyl cations. J. Org. Chem. 44 (1979) 1704-1708.
9. Korolev, B. A.; Solodar, S. L.; Vinogradov, L. M.; Kochkin, V. A.: Reactions of polycyclic ketones. XVIII. Basicity and protonation site of aminophenalenones. Zh. Org. Khim. (Rus.) 16 (1980) 2128-2137.
10. Kuznetsova, N. A.; Kaliya, O. L.; Ioffe, N. G.; Solodar, S. L.: Radical formation in photolysis of phenalenone and its amino derivatives. Zh. Obschch. Khim. (Rus.) 55 (1985) 389-391.
11. Akopyan, M. E.; Kaliya, O. L.; Kuznetsova, N. A.; Petrachenko, N. E.; Savvina, L. P.; Solodar, S. L.; Timoshenko, M. M.; Chizhov, Yu. V.: Photoelectron spectroscopy of aminophenalenones: correlation of electronic structure with the photostability of ethanol solutions. Khim. Vys. Energ. (Rus.) 18 (1984) 520-526.
12. Bushuk, B. A.; Rubinov, A. N.; Berestov, A. L.: Rotational diffusion of neutral and cationic forms of 6-aminophenalenone in solutions. Khim. Fiz. (Rus.) 9 (1900) 1558-1563.
13. 9NO. Z. Kristallogr. 211 (1996) 942.
14. 10ClNO. Z. Kristallogr. 211 (1996) 943-944.
15. Haddon, R. C.; Chichester, S. V.; Mayo, S. L.: Direct amination of 9-hydroxy-l-oxophenalene to produce 9-amino-l-oxophenalene and related compounds. Synthesis (1985) 639-641.
16. Solodar, S. L.; Kochkin, V. A.: Reactions of polycyclic ketones. XIX. Nitration of 2-aminophenalenone. Zh. Org. Khim. (Rus.) 16 (1980) 2137-2141.
17. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israél. R.; Smits, J. M. M.: The DIRDIF Program System. Technical Report. Crystallography Laboratory, University of Nijmegen, The Netherlands 1994.
18. Sheldrick, G. M.: SHELXL-93. Program for the Refinement of Crystal Structures. University of Göttingen. Germany 1993.
19. Stewart, J. J. P.: MOPAC6.0. QCPE program No. 455. Department of Chemistry, Indiana University, Bloomington, USA 1990.
20. Smith, D. A.; Ulmer, C. W.; Gilbert, M. J.: Structural studies of aromatic amines and the DNA intercalating compounds m-AMSA and o-AMSA: comparison of MNDO, AM1, and PM3 to experimental and ab initio results. J. Comput. Chem. 13 (1992) 640-650.
21. Morley, J. O.: Effect of molecular conformation on the electronic properties of donoracceptor azobenzenes. J. Chem. Soc. Faraday Trans 91 (1995) 2067-2069.
22. Klamt, A.; Schüürmann, G.: COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J. Chem. Soc. Perkin Trans 2 (1993) 799-805.
23. Dick, B.; Hohlneicher, G.: Two-photon spectroscopy of dipole-forbidden transitions. I. Dipole-forbidden transitions and double excited configurations in the CNDO-CI methods. Theor. Chim. Acta 53 (1979) 221-251.
24. Dick, B.; Nickel, B.: Accessibility of the lowest quintet state of organic molecules through triplet-triplet annihilation. Chem. Phys. 78 (1983) 1-16.
25. Tafeenko, V. A.; Solodar, S. L.; Medvedev, S. V.: X-ray crystal structures of 2-(acetylamino)phenalenone and benzanthrone. Zh. Obschch. Khim. (Rus.) 58 (1988) 2600-2605.
26. Voloshin, N. A.; Tikhonova, M. E.; Furmanova, N. G.; Lesin, A. V.; Andrianov, V. I.; Borisenko, N. I.; Ryskina, T. A.; Zhdanov, Yu. A.; Minkin, V. I.; Olekhnovich, L. P.: Acylotropic tautomerism. XXIX. Arylo- and heteroarylotropism of 9-hydroxyphenalenone O-derivatives. Zh. Org. Khim. (Rus.) 26 (1990) 1817-1829.
27. Lesin, A. V.; Furmanova, N. G.; Shishova, T. G.; Tikhonova, M. E.; Voloshin, N. A.; Zhdanov, Yu. A.; Olekhnovich, L. P.: Acylotropic tautomerism. XXXIV. Variability of the conjugation and conformation of the reactive moiety of 9-(aroyloxy)phenalenones. Zh. Org. Khim. (Rus.) 27 (1991 ) 1162-1172.
28. Olekhnovich, L. P.; Tikhonova, M. E.; Voloshin, N. A.; Furmanova, N. G.; Lesin, A. V.; Kompan, O. E.; Borisenko, N. I.; Zeimakh, I. D.; Minkin, V. I.; Zhdanov, Yu. A.: Acylotropic tautoinerism. XXVIII. Correlation of kinetics and mechanism of intramolecular transaroylation with structure and conformation of the benzoyl migrant in 9-hydroxyphenalenone O-derivatives. Topology of aroylotropy. Zh. Org. Khim. (Rus.) 26 (1990) 476-487.
29. Johnson, S. W.; Eckert, J.: Barthes, M.; McMullan, R. K.; Muller, M.: Crystal structure of acetanilide at 15 and 295 K by neutron diffraction. Lack of evidence for proton transfer along the N-H . . . O hydrogen bond. J. Phys. Chem. 99 (1995) 16253-16260.
30. Bertolasi, V.; Nanni, L.; Gilli, P.; Ferretti, V.; Gilli, G.; Issa, Y. M.; Sherif, O. E.: Intramolecular N-H . . . O=C hydrogen bonding assisted by resonance. Intercorrelation between structural and spectroscopic data for six β-diketo-arylhydrazones derived from benzoylacetone or acetylacetone. New J. Chem. 18 (1994) 251-261.
31. Negrebetskii, V. V.; Reznichenko, A. V: Electronic structure and reactivity of carbonyl compounds. I. Features of protonation of some substituted polycyclic aromatic ketones. Zh. Obschch. Khim. (Rus.) 64 (1994) 1510-1515.
32. Pagni, R. M.; Peebles, W.; Haddon, R. C.; Chichester, S. V.: The role of substituents on carbodication stability. J. Org. Chem. 55 (1900) 5595-5601.
33. Allen, F. H.; Kennard, O.: 3D search and research using the Cambridge Structural Database. Chem. Design Automation News 8 (1993) 1, 31-37.
34. Rubinov, A. N.; Bushuk, B. A.; Stupak, A. P.; Berestov, A. L.: Picosecond spectroscopy of specific solvalion of dye molecules in solutions. Izv. Akad. Nauk SSSR, ser Fiz. (Rus.) 53 (1989) 793-798.
35. Aladov, A. V.; Rylkov, V. V.; Reznichenko, A. V.; Kokin, V. N.; Gorelik, A. V.; Lukyanels, E. A.: Spectral characteristics of excited slates of aminophenalenones in ethanol. Opt. Spektr. (Rus.) 64 (1988) 51-56.
36. Reichardt, C.: Solvents and Solvent Effects in Organic Chemistry. Verlag Chemie, Weinheim 1988.
37. Suppan, P.: Solvatochromic shifts: the influence of the medium on the energy of electronic states. J. Photochem. Photobiol. 50 (1990) 293-330.
38. Ríos, M. A.; Rodríguez, J.: Semiempirical study of compounds with O-H- O intramolecular hydrogen bond. J. Comput. Chem. 13 (1992) 860-866.
39. McArdle, P.: SORTX - a program for on-screen stick-model editing and autosorting of SHELX files for use on a PC. J. Appl. Crystallogr. 28 (1995) 65.