DFT studies on tautomeric preferences of 1-(pyridin-2-yl)- 4-(quinolin-2-yl)butane-2,3-dione in the gas phase and in solution

Structural Chemistry

Volumn 21, Issue 6, 2010, Pages 1283-1287

  Dobosz, Robert ^a   Gawinecki, Ryszard ^a   Ośmiałowski, Borys ^a  

^a UNIVERSITY OF TECHNOLOGY AND LIFE SCIENCES   (Poland)

Author keywords

DFT calculations; Intramolecular hydrogen bond; Solvent effect; Tautomerism; Diketones

Indexed keywords

EID: 84962427393     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11224-010-9674-y     Document Type: Article

References (23)

1. Katritzky AR (1965) Chem Ind (London) 331-335
2. Kolehmainen E, Ośmialowski B, Krygowski TM, Kauppinen R, Nissinen M, Gawinecki R (2000) J Chem Soc Perkin Trans 2: 1259-1266
3. Konno Sh, Shiraiwa M, Yamanaka H (1981) Chem Pharm Bull 29:3554-3560
4. Gnichtel H, Möller B (1981) Liebigs Ann Chem 1751-1759
5. Gawinecki R, Kolehmainen E, Loghmani-Khouzani H, Ośmialowski B, Lovász T, Rosa P (2006) Eur J Org Chem 2817-2824
6. Ośmialowski B, Kolehmainen E, Nissinen M, Krygowski TM, Gawinecki R (2002) J Org Chem 67:3339-3345
7. Ośmialowski B, Kolehmainen E, Gawinecki R (2003) Chem Eur J 9:2710-2716
8. Dobosz R, Gawinecki R (2010) J Mol Struct (Theochem) 940:119-123
9. Dobosz R, Gawinecki R, Kanabaj A (2010) J Mol Struct (Theochem) 949:57-59
10. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, 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, Bakken V, 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 (2004) Gaussian 03 Revision E01 Inc. Gaussian, Wallingford
11. Becke AD (1993) J Chem Phys 98:1372-1377
12. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785-789
13. Miertus S, Tomasi J (1982) Chem Phys 65:239-245
14. Miertus S, Scrocco E, Tomasi J (1981) Chem Phys 55:117-129
15. Raczyńska ED, Kosińska W, Ośmialowski B, Gawinecki R (2005) Chem Rev 105:3561-3612
16. Krygowski TM (1993) J Chem Inf Comput Sci 33:70-78
17. Sobczyk L, Grabowski JS, Krygowski TM (2005) Chem Rev 105:3513-3560
18. Clar E (1964) Polycyclic hydrocarbons, vols 1 and 2. Academic Press, London
19. Clar E (1972) Aromatic sextet. Wiley, London
20. Gilli G, Bellucci F, Ferretti V, Bertolasi V (1989) J Am Chem Soc 111:1023-1028
21. Bertolasi V, Gilli P, Ferretti V, Gilli G (1991) J Am Chem Soc 113:4917-4925
22. Gilli P, Bertolasi V, Ferretti V, Gilli G (1994) J Am Chem Soc 116:909-915
23. Bertolasi V, Gilli P, Ferretti V, Gilli G (1996) Chem Eur J 2:925-934