A joint theoretical and experimental investigation on the 13C and 1H NMR chemical shifts of coumarin derivatives

Theoretical Chemistry Accounts

Volumn 125, Issue 3-6, 2010, Pages 461-470

  d'Antuono, Philippe ^a,c   Botek, Edith ^a   Champagne, Benoît ^a   Maton, Laetitia ^b   Taziaux, Dorothée ^b   Habib Jiwan, Jean Louis ^b  

^a UNIVERSITY OF NAMUR   (Belgium)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^c UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

Chemical shift; Conformation impact and Maxwell Boltzmann averaging; Coumarin derivatives; Coupled perturbed Kohn Sham; Solvent effects on the chemical shift

Indexed keywords

EID: 77949273387     PISSN: 1432881X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00214-009-0625-x     Document Type: Article

References (44)

1. Helgaker T, Jaszunski M, Ruud K (1999) Chem Rev 99: 293.
2. Gauss J, Stanton JF (2002) Adv Chem Phys 123: 355.
3. Kaupp M, Bühl M, Malkin VG (eds) (2004) Calculation of NMR and EPR parameters. Wiley-VCH, Weinheim.
4. Bagno A, Rastrelli F, Saielli G (2006) Chem Eur J 12: 5514.
5. Bifulco G, Dambruoso P, Gomez-Paloma L, Riccio R (2007) Chem Rev 107: 3744.
6. Ando I, Kuroki S, Kurosu H, Yamanobe T (2001) Prog NMR Spectrosc 39: 79.
7. d'Antuono Ph, Botek E, Champagne B, Wieme J, Reyniers M-F, Marin GB, Adriaensens PJ, Gelan JM (2007) Chem Phys Lett 436: 388.
8. Chesnut DB (1996) The ab initio computation of nuclear magnetic resonance chemical shielding. In: Lipkowitz KB, Boyd DB (eds) Reviews in computational chemistry, vol 8. VCH, Weinheim, p 245.
9. Rablen PR, Pearlman SA, Finkbiner J (1999) J Phys Chem A 103: 7357.
10. d'Antuono Ph, Botek E, Champagne B, Spassova M, Denkova P (2006) J Chem Phys 125: 144309.
11. Bifulco G, Gomez-Paloma L, Riccio R (2003) Tetrahedron Lett 44: 7137.
12. Trabelsi M, Salem M, Champagne B (2003) Org Biomol Chem 1: 3839.
13. Poater J, van Lenthe E, Baerends EJ (2003) J Chem Phys 118: 8584.
14. Allen MJ, Keal TW, Tozer DJ (2003) Chem Phys Lett 380: 380.
15. Tähtinen P, Bagno A, Klika KD, Pihlaja K (2003) J Am Chem Soc 125: 4609.
16. Hieringer W, Della Sala F, Görling A (2004) Chem Phys Lett 383: 115.
17. Arbuznikov AV, Kaupp M (2004) Chem Phys Lett 386: 8.
18. Gryffer-Keller A, Molchanov S (2004) Mol Phys 102: 1903.
19. Wiitala KW, Hoye TR, Cramer CJ (2006) J Chem Theor Comput 2: 1085.
20. Wiitala KW, Al-Rashid ZF, Dvornikovs V, Hoye TR, Cramer CJ (2007) J Phys Org Chem 20: 345.
21. Wiitala KW, Cramer CJ, Hoye TR (2007) Magn Reson Chem 45: 819.
22. Rychnovsky SD (2006) Org Lett 8: 2895.
23. Bagno A, Rastrelli F, Saielli G (2007) J Org Chem 72: 7373.
24. Pennanen TS, Lantto P, Sillanpää AJ, Vaara J (2007) J Phys Chem A 111: 182.
25. Bassarello C, Bifulco G, Montoro P, Skhirtladze A, Kemertelidze E, Pizza C, Piacente S (2007) Tetrahedron 63: 148.
26. Baldridge KK, Siegel JS (2008) Theor Chem Acc 120: 95.
27. Habib-Jiwan J-L, Branger C, Soumillon J-Ph, Valeur B (1998) J Photochem Photobiol A Chem 116: 127.
28. Leray I, Habib-Jiwan J-L, Branger C, Soumillon JPh, Valeur B (2000) J Photochem Photobiol A Chem 135: 163.
29. Taziaux D, Soumillon J-Ph, Habib-Jiwan J-L (2004) J Photochem Photobiol A Chem 162: 599.
30. Maton L, Taziaux D, Soumillion J-Ph, Habib Jiwan J-L (2005) J Mater Chem 15: 2928.
31. Löhr HG, Vögtle F (1985) Acc Chem Res 18: 65.
32. Valeur B (2001) Molecular fluorescence: principles and applications. Wiley-VCH Verlag GmbH, Weinheim.
33. Fedorova OA, Fedorov YV, Vedernikov AI, Gromov SP, Yescheulova OV, Alfimov MV, Woerner M, Bossmann S, Braun A, Saltiel J (2002) J Phys Chem A 106: 6213.
34. Korolev VV, Vorobyev DYu, Glebov EM, Grivin VP, Plyusnin VF, Koshkin AV, Fedorova OA, Gromov SP, Alfimov MV, Shklyaev YV, Vshivkova TS, Rozhkova YS, Tolstikov AG, Lokshin VV, Samat A (2007) J Photochem Photobiol A Chem 192: 75.
35. Berthet J, Micheau JC, Lokshin V, Vales M, Vermeersch G, Delbaere S (2008) Org Lett 10: 3773.
36. Ditchfield R (1971) J Am Chem Soc 93: 5287.
37. Wolinski K, Hilton JF, Pulay P (1990) J Am Chem Soc 112: 8251.
38. Cammi R, Mennucci B, Tomasi J (1999) J Chem Phys 110: 7627.
39. Manalo MN, de Dios AC, Cammi R (2000) J Phys Chem A 104: 9600.
40. Tomasi J, Mennucci B, Cammi R (2005) Chem Rev 105: 2999.
41. 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, 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 C. 02. Gaussian, Inc., Wallingford.
42. Filatov M, Cremer D (2005) J Chem Phys 123: 124101.
43. d'Antuono Ph, Botek E, Champagne B, Wieme J, Reyniers M-F, Marin GB, Adriaensens PJ, Gelan JM (2005) Chem Phys Lett 211: 207.
44. d'Antuono Ph, Botek E, Champagne B, Wieme J, Reyniers M-F, Marin GB, Adriaensens PJ, Gelan JM (2008) J Phys Chem B 112: 14804.