Computation and analysis of 19F substituent chemical shifts of some bridgehead-substituted polycyclic alkyl fluorides

Magnetic Resonance in Chemistry

Volumn 41, Issue 7, 2003, Pages 503-508

  Adcock, William ^a   Peralta, Juan E ^b   Contreras, Ruben H ^b  

^a FLINDERS UNIVERSITY   (Australia)

^b UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

19F chemical shift; Bridgehead substituted bicyclic fluorides; DFT GIAO; DFT NBO; Hyperconjugative interactions; NMR; Substituent effects

Indexed keywords

CHEMICAL BONDS; CHEMICAL SHIFT; COMPUTATION THEORY; ELECTRONEGATIVITY; FLUORINE COMPOUNDS; REGRESSION ANALYSIS;

19F CHEMICAL SHIFT; ALKYL FLUORIDES; BRIDGEHEAD-SUBSTITUTED BICYCLIC FLUORIDE; DFT-NATURAL BOND ORBITAL; DFT/GIAO; HYPERCONJUGATIVE INTERACTIONS; LONE PAIR; MOLECULAR PARAMETERS; NATURAL BOND ORBITAL; SUBSTITUENT EFFECT;

FLUORINE;

BRIDGED COMPOUND; CARBON; FLUORIDE; FLUORINE; POLYCYCLIC HYDROCARBON;

ARTICLE; CHEMICAL BOND; ELECTROMAGNETIC FIELD; ELECTRON; GEOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARAMETER; RIGIDITY; SUBSTITUTION REACTION; THEORETICAL MODEL;

EID: 0038801545     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/mrc.1202     Document Type: Article

References (44)

1. Ebraheem KAK, Webb GA. Prog. Nucl. Magn. Reson. Spectrosc. 1977; 11: 149, and references cited therein.
2. Gakh YG, Gakh AA, Gronenbom AM. Magn. Reson. Chem. 2000; 38: 551, and references cited therein.
3. Adcock W, Lunsmann D, Peralta JE, Contreras RH. Magn. Reson. Chem. 1999; 37: 167.
4. (a) Wiberg KB, Zilm KW. J. Org. Chem. 2001; 66: 2809;
5. (b) Lau EY, Gerig JT. J. Am. Chem. Soc. 2000; 122: 4408;
6. (c) Shtarev AB, Pinkhassik E, Levin MD, Stibor I, Michl J. J. Am. Chem. Soc. 2001; 123: 3484;
7. (d) Tanuma T, Irisawa J. J. Fluorine Chem. 1999; 99: 157;
8. (e) Tanuma T, Irisawa J, Ohnishi K. J. Fluorine Chem. 2000; 102: 205.
9. Reynolds WF. Prog. Phys. Org. Chem. 1983; 14: 165, and references cited therein.
10. Craik DJ. Annu. Rep. NMR Spectrosc. 1983; 15: 1, and references cited therein.
11. (a) Saika A, Slichter CP. J. Chem. Phys. 1954; 22: 26;
12. (b) Emsley JW, Feeney J, Sutcliffe LH. High-resolution Nuclear Magnetic Resonance Spectroscopy. Pergamon Press: Oxford, 1965; Chapt. 4.
13. Hansch C, Leo A, Taft RW. Chem. Rev 1991; 91: 165, and references cited therein.
14. Hehre WJ, Taft RW, Topsom RD. Prog. Phys. Org. Chem. 1976; 12: 159.
15. (a) Adcock W, Abeywickrema AN. J. Org. Chem. 1982; 47: 2957;
16. (b) Adcock W, Abeywickrema AN, Kok GB. J. Org. Chem. 1984; 49: 1387;
17. (c) Adcock W, Iyer VS. J. Org. Chem. 1985; 50: 1538;
18. (d) Adcock W, Kok GB J. Org. Chem. 1987; 52: 356;
19. (e) Adcock W, Iyer VS. J. Org. Chem. 1988; 53: 5259;
20. (f) Adcock W, Trout NA. J. Org. Chem. 1991; 56: 3229;
21. (g) Della EW, Head NJ. J. Org. Chem. 1995; 60: 5303;
22. (h) Adcock W, Trout NA. Magn. Reson. Chem. 1998; 36: 181;
23. (i) Adcock W, Trout NA. Chem. Rev. 1999; 99: 1415, and references cited therein;
24. (j) Adcock W, Krstic AR. Magn. Reson. Chem. 2000; 38: 115.
25. Reed AE, Curtiss LA, Weinhold F. Chem. Rev. 1988; 88: 899.
26. Becke AD. J. Chem. Phys. 1993; 98: 5648.
27. (a) Wolinski K, Hinton JF, Pulay P. J. Am. Chem. Soc. 1990; 112: 8251;
28. (b) Cheeseman JR, Trucks GW, Keith TA, Frisch MJ. J. Chem. Phys. 1996; 104: 5497.
29. (a) Reed AE, Curtis LA, Weinhold F. Chem. Rev. 1988; 88: 899;
30. (b) Weinhold F. In Encyclopedia of Computational Chemistry, vol. 3, Schleyer PvR (ed.). Wiley: New York, 1998; 1792.
31. Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BG, Robb MA, Cheeseman JR, Keith T, Petersson GA, Montgomery JA, Raghavachari K, Al-Laham MA, Zakrzewski VG, Ortiz JV, Foresman JB, Cioslowski J, Stefanov BB, Nanayakkara A, Challacombe M, Peng CY, Ayala PY, Chen W, Wong MW, Andres JL, Replogle ES, Gomperts R, Martin RL, Fox DJ, Binkley JS, Defrees DJ, Baker J, Stewart JP, Head-Gordon M, Gonzalez C, Pople JA. Gaussian 94, Revision D.3. Gaussian: Pittsburgh, PA, 1995.
32. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Rega N, Salvador P, Dannenberg JJ, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, Revision A.11.3. Gaussian: Pittsburgh, PA, 2002.
33. Adcock W, Abeywickrema AN, Iyer VS, Kok GB. Magn. Reson. Chem. 1986; 24: 213.
34. Adcock W, Gangodawila H, Kok GB, Iyer VS, Kitching W, Drew GM, Young D. Organometallics 1987; 6: 156.
35. Marriott S, Topsom RD. J. Am. Chem. Soc. 1984; 106: 7.
36. Marriott S, Reynolds WF, Taft RW, Topsom RD. J. Org. Chem. 1984; 49: 959.
37. (a) Nolan EM, Linck RG. J. Am. Chem. Soc. 2000; 122: 11497, and references cited therein;
38. (b) Gross KC, Seybold PG. J. Org. Chem. 2001; 66: 6919, and references cited therein.
39. Taft RW, Topsom RD. Prog. Phys. Org. Chem. 1987; 16: 1.
40. Wiberg KB. J. Org. Chem. 2002; 67: 1613.
41. Augspurger JD, Dykstra CE. J. Am. Chem. Soc. 1993; 115: 12016.
42. Adcock W, Abeywickrema AN. J. Org. Chem. 1982; 47: 2945.
43. Koppell IA, Mishima M, Stock LM, Taft RW, Topsom RD. J. Phys. Org. Chem. 1993; 6: 685.
44. Maerker C, Schleyer PvR, Liedl KR, Ha T-K, Quack M, Suhm MA. J. Comput. Chem. 1997; 18: 1695, and references cited therein.