Conformer determination of stabilized triphenyl phosphonium acyl ylides by infrared spectroscopy

Journal of Molecular Structure

Volumn 921, Issue 1-3, 2009, Pages 6-12

  Bunton, Clifford A ^a   Silva, Paul ^b   Castañeda, Fernando ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CHILE   (Chile)

Author keywords

Acyl stretching frequencies; Cyano stretching frequencies; HF and DFT calculations; Triphenyl phosphonium ylides; Ylidic conformation

Indexed keywords

ESTERIFICATION; ESTERS; INFRARED SPECTROSCOPY; KETONES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS; PROBABILITY DENSITY FUNCTION; SPECTROSCOPIC ANALYSIS; SULFUR COMPOUNDS;

ACYL STRETCHING FREQUENCIES; CYANO STRETCHING FREQUENCIES; HF AND DFT CALCULATIONS; TRIPHENYL PHOSPHONIUM YLIDES; YLIDIC CONFORMATION;

X RAY CRYSTALLOGRAPHY;

EID: 60749092743     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2008.12.016     Document Type: Article

References (39)

1. Cristau H.J., and Plenat F. In: Hartley F.R. (Ed). The Chemistry of Organophosphorus Compounds vol. 3 (1994), Wiley, New York 108 (Chapter 2)
2. Bachrach S.M., and Nitsche C.I. In: Hartley F.R. (Ed). The Chemistry of Organophosphorus Compounds vol. 3 (1994), Wiley, New York 273 (Chapter 4)
3. Wilson I.F., and Tebby J.C. J. Chem. Soc. Perkin Trans. 2 (1972) 31
4. Wilson I.F., and Tebby J.C. Tetrahedron Lett. (1970) 3769
5. Zeliger H.I., Snyder J.P., and Bestmann H.J. Tetrahedron Lett. (1969) 2199
6. Zeliger H.I., Snyder J.P., and Bestmann H.J. Tetrahedron Lett. (1970) 3313
7. Gray G.A. J. Am. Chem. Soc. 95 (1973) 7736
8. Randall F.J., and Johnson A.W. Tetrahedron Lett. (1968) 2841
9. Albright T.A., Gordon M.D., Freeman W.J., and Schweizer E.E. J. Am. Chem Soc. 98 (1976) 6249
10. Castañeda F., Terraza C.A., Bunton C.A., Gillitt N.D., and Garland M.T. Phosphorus Sulfur Silicon 178 (2003) 1973
11. Castañeda F., Recabarren G.I., Hu J., Gillitt N.D., and Bunton C.A. Phosphorus Sulfur Silicon 178 (2003) 2505
12. Castañeda F., Aliaga C., Garland M.T., Hu J., Gillitt N.D., and Bunton C.A. Phosphorus Sulfur Silicon 182 (2007) 151
13. Castañeda F., Jullian C., Bunton C.A., Garland M.T., and Baggio R. Acta Crystallogr. C 63 (2007) 267
14. Castañeda F., Silva P., Garland M.T., Shirazi A., and Bunton C.A. Phosphorus Sulfur Silicon 184 (2009) 19
15. Kobayashi M., Sanda F., and Endo T. Macromolecules 33 (2000) 5384
16. Bachrach S.M. J. Org. Chem. 57 (1992) 4367
17. Abell A.D., Clark B.M., and Robinson W.T. Aust. J. Chem. 42 (1989) 1161
18. Castañeda F., Terraza C.A., Garland M.T., Bunton C.A., and Baggio R. Acta Crystallogr. C 57 (2001) 180
19. Castañeda F., Silva P., Bunton C.A., Garland M.T., and Baggio R. Acta Crystallogr. C 64 (2008) 405
20. Castañeda F., Aliaga C., Bunton C.A., Garland M.T., and Baggio R. Acta Crystallogr. C 61 (2005) 496
21. Cramer C.J. Essentials of Quantum Chemistry (2002), Wiley, New York (Chapter 9)
22. Castañeda F., Acuña C., Garland M.T., Gillitt N.D., Shirazi A., Yunes S.J., and Bunton C.A. Phosphorus Sulfur Silicon 182 (2007) 2541
23. Castañeda F., Bunton C.A., Baggio R., and Garland M.T. Acta Crystallogr. C 63 (2007) 65
24. Eliel E.L., and Wilen S.H. Stereochemistry of Organic Compounds (1994), Wiley, New York p. 635, 641
25. T. Shimanouchi, Tables of Molecular Vibrational Frequencies, vol. 1, NSRDS-NBS 39, National Bureau of Standards, Washington, DC, 1972.
26. Scott A.P., and Radom L. J. Phys. Chem. 100 (1996) 16502
27. Bose P.K., and Polavarapu P.L. Chem. Phys. Lett. 155 (1989) 39
28. Wong M.W. Chem. Phys. Lett. 256 (1996) 391
29. Jones G.I.L., and Owen N.L. J. Mol. Struct. 18 (1973) 1
30. Riveros J.M., and Wilson E.B. J. Chem. Phys. 46 (1967) 4605
31. Eliel E.L., and Wilen S.H. Stereochemistry of Organic Compounds (1994), Wiley, New York p. 618
32. Horner L., and Oediger H. Chem. Ber. 91 (1958) 437
33. Hehre W.J. A Guide to Molecular Mechanics and Quantum Chemical Calculations (2003), Wavefunction Inc., Irvine (Chapter 5)
34. Nishio M., Umezawa Y., Hirota M., and Takeuchi Y. Tetrahedron 51 (1995) 8665
35. Nishio M., and Hirota M. Tetrahedron 45 (1989) 7201
36. Desiraju G.R., and Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology (1999), Oxford University Press p. 152
37. F. Castañeda, P. Silva, M.T. Garland, A. Shirazi, C.A. Bunton, Phosphorus, Sulfur Silicon, in press.
38. Prasad R.L., Kushwaha A., Suchita, Kumar M., and Yadav R.A. Spectrochim. Acta A 69 (2008) 304
39. Kumar S., Rai A.K., Rai S.B., Rai D.K., Singh A.N., and Singh V.B. J. Mol. Struct. 791 (2006) 23