Synthesis and structural study of 2′- and 2′,6′- positioned methyl- and nitro-substituted 3-(arylhydrazono)pentane-2,4-diones

Journal of Physical Organic Chemistry

Volumn 20, Issue 10, 2007, Pages 716-731

  Marten, Jan ^a   Seichter, Wilhelm ^a   Weber, Edwin ^a   Böhme, Uwe ^a  

^a TU BERGAKADEMIE FREIBERG   (Germany)

Author keywords

3 (arylhydrazono)pentane 2,4 diones; Crystal structures; DFT calculations; Synthesis

Indexed keywords

CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; METHANE; NITROGEN; QUANTUM CHEMISTRY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

3-(ARYLHYDRAZONO)PENTANE-2,4-DIONES; DFT CALCULATIONS; ROTATIONAL BARRIERS; X-RAY CRYSTAL STRUCTURE ANALYSIS;

KETONES;

EID: 35349028388     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1225     Document Type: Review

References (42)

1. Phillips RR. Org. React. 1959; 10: 143-178.
2. Bertolasi V, Ferretti V, Gilli P, Gilli G, Issa YM, Sherif OM. J. Chem. Soc., Perkin Trans. 2 1993; 2223-2228.
3. Marten J, Seichter W, Weber E. Z Anorg. Allg. Chem 2005; 631: 869-877.
4. Albert J, Gonzales A, Granell J, Moragas R, Puerta C, Valerla P. Organometallics 1997; 16: 3775-3778.
5. Mishra L, Yadaw AK, Srivastava S. New J. Chem. 2000; 24: 505-510.
6. Kuzmina NP, Eliseeva SV, Balashov AM, Trojanov SI. Z Neorg. Chim. Moscow 2002; 47: 1300-1304.
7. Sharma G. J. Med. Chem. 1969; 12: 1122-1124.
8. Bertolasi V, Nanni L, Gilli P, Ferretti V, Gilli G. New. J. Chem. 1994; 18: 251-261.
9. Yao HC. J. Chem. Soc. 1964; 2959-2963.
10. Rappoport H. The Chemistry of Enols. Wiley: New York, 1990.
11. Gilli P, Bertolasi V, Pretto L, Lyčka A, Gilli G. J. Am. Chem. Soc. 2002; 124: 13554-13567.
12. McVie J, Alastair D, Sinclair RS, Truscott TG. J. Chem. Soc. Perkin Trans. 1980; 2: 286-290.
13. Püttner R. In Methoden der Organischen Chemie. (Houben-Weyl), vol. 10/3: 1965; p. 1.
14. Gilli G, Belucci F, Ferretti V, Bertolasi V. J. Am. Chem. Soc. 1989; 111: 1023-1028.
15. Elguero J, Mo O, Yanez M, del Bene JE. Mol. Phys. 2004; 102: 2563-2571.
16. Grabowski SJ. J. Phys. Org. Chem. 2003; 16: 797-802.
17. Sanchez AG, de Gracia M, Garcia M, Borrachero P, Bellanato J. J. Chem. Soc., Perkin Trans. 2 1987; 301-306.
18. Gawinecki R, Kolehmainen E, Janota H, Kauppinen R, Nissinen M, Osmialowski B. J. Phys. Org. Chem. 2001; 14: 797-803.
19. Hehre WJ, Radom L, Schleyer PR, Pople JA. Ab Initio Molecular Orbital Theory. J. Wiley & Sons: Chichester, 1986.
20. The rotational barriers in nitrobenzol and other aromatic nitro compounds have been investigated before; for further details see: Chen PC, Chen SC, Int. J. Quantum Chem. 2001; 83: 332-337.
21. Gilli P, Bertolasi V, Ferretti V, Gilli G. J. Am. Chem. Soc 2000; 122: 10405-10417.
22. Bader RFW. Atoms in Molecules. Clarendon Press: Oxford, 1994.
23. Gillespie RJ. J. Chem Educ. 2001; 78: 1688-1690.
24. Explanation taken from: Gillespie RA, Popelier PLA, Chemical Bonding and Molecular Geometry. Oxford University Press: New York, 2001.
25. Matta CF, Hernández-Trujillo J, Tang TH, Bader RFW. Chem. Eur. J. 2003; 9: 1940-1951.
26. Poater J, Solà M, Bickelhaupt FM. Chem. Eur. J. 2006; 12: 2889-2895.
27. Bader RFW. Chem. Eur. J. 2006; 12: 2896-2901.
28. Poater J, Sola M, Bickelhaupt FM. Chem. Eur. J. 2006; 12: 2902-2905.
29. Espinosa E, Souhassou M, Lachekar H, Lecomte C. Acta Cryst. 1999; B55: 563-572.
30. Aydeniz Y, Oguz F, Yaman A, Konuklar AS, Dogan I, Aviyente V, Klein RA. Org. Biomol. Chem. 2004; 2: 2426-2436.
31. McCleverty JA, Meyer TJ, Fujita M, Powell A, Creutz CA. Comprehensive Coordination Chemistry. Elsevier: Oxford, 2004.
32. Ho YW, Wang U. Dyes Pigments 1995; 29: 295-304.
33. Bruker Analytical X-ray, Systems. SAINT-NT (Version 6.0), 2003.
34. Sheldrick GM. SHELX-97, Program for Crystal Structure Solution and Refinement. University of Göttingen: Germany, 1997.
35. Gaussian 03, Revision C.02, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, 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 JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian, Inc.: Wallingford CT, 2004.
36. Becke AD. J. Chem. Phys. 1993; 98: 5648-5652.
37. Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ. J. Phys. Chem. 1994; 98: 11623-11627.
38. Hariharan PC, Pople JA. Theoret. Chimica Acta. 1973; 28: 213-222.
39. Franci MM, Pietro WJ, Hehre WJ, Binkley JS, Gordon MS, DeFrees DJ, Pople JA. J. Chem. Phys. 1982; 77: 3654-3665.
40. Hobza P. Annu. Rep. Prog. Chem., Sect. C 2004; 100: 3-27.
41. GaussView 3.0, Gaussian Inc., Pittsburgh 2004.
42. Popelier LA. Comput. Phys. Commun. 1998; 108: 180-190.