conformational properties and the anomeric effect study of phosphinanes

Subject Areas :

Javad Azizian ¹ , Mahdieh Entezari ² , Hossein Anaraki Ardakani ³ , Shahab Zomorodbakhsh ⁴

1 - Department of chemistry, Science and Reaserch branch, Islamic azad university, Tehran, Iran
2 - Department of chemist r,y Mahshahr branch, Islamic azad university, Mahshahr, Iran
3 - Department of chemist r,y Mahshahr branch, Islamic azad university, Mahshahr, Iran
4 - Department of chemist r,y Mahshahr branch, Islamic azad university, Mahshahr, Iran

Received: 2014-06-15 Accepted : 2014-08-15 Published : 2014-09-01

Keywords: bond length, anomeric effect, 2- phosphinane, axial and equatorial position, Ab initio calculations,

Abstract :

Ab initio HF/6-31G* Methode was employed to calculate the bond length in 2- phosphinanes when electronegative groups was at C-2 tend axial and equatorial positions. The magnitude of the anomeric effect depends on the nature of the substituent, the effect of the substituent can be seen by comparing the bond length in 2-chloro and 2- boromo substituented phosphinanes. The effect of anomeric effect have been effected on the bond length in 2-phosphinanes.

References:

[1] C.L, Perrin, K. B, Armstrong, M. A, Fabian: J. Am. Chem. Soc. 116, 1994, pp. 715-722.
[2] Chu N, J. Ph.D Thesis, university of Ottawa, 1959.
[3] R. U, Lemieux, Chu, N. J. Abstracts of papers, 133th national meeting of the American
Chemical society; Washington, DC, 1958, Abstr. 31N.
[4] E, Juaristi; G, Cuevas: Tetrahedron 48 (1992) 5019.
[5] A. J Kirby: Springer Verlag, Berlin, (1983).
[6] R. U, Lemieux. In Molecular Rearrangement; P. De Mayo, Ed: Interscience, New York,
(1964), pp. 723.
[7] W. A. Szarek, D. Horton, the anomeric effect: Origin and Consequences, ACS Symposium
series no. 87, American Chemical Society, Washington D.C, (1979).
[8] S. Wolfe, A. Rauk, L. M. Tel, I. G. Csizmaida, J. Chem. Soc. B: 136 (1971). Eisenstein, W. J.
Hehre, L. salem, R. Hoffmann: J. Am. Chem. Soc: 95 (1973) 306.
[9] M J. Gallager, phosphorus 31-NMR spectroscopy in Stereochemical Analysis, edited by J G.
Verkade , L D. Quin, 1987, Chapter9.
[10] W. E. McEwen , K. D. Berlin,

[12] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman,
V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Jr. Burant, S Dapprich., J. Millam,
V. Barone, M. Cossi, R. Cammi, B. Mennucci C. Pomelli, C. Adamo, S. Clifford, j. Ochterski,
G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K.
Raghavachari, J. B. Foresman, j. Cioslowski, J. V. Ortiz, B. tefanovb, G. Liu, A. Liashenko, P.
Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A Al-Laham. C. Y.
Peng, A Nanayakkara., C. Gonzalez, M. Challacombe, P. M. W. Gill, B .Johnson, W.Chen, M.
W.Wong, J. L Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, GAUSSIAN 98 (Revision
A. 3) Gaussian Inc., Pittsburgh, PA, (1998).