The Linear Relation Between the Molar Rotation and the Helical Radius and Pitch

• Autorzy: Zhou X. M. , Hou R. Y. , Fu H. , Ma K. S. , Zhou Z. Y. , Zhang A. G.
• Języki publikacji: EN

Abstrakty

EN

Gas station ary conformers of lactic acid and its deriva tives (F, Cl, Br and CN replace OH) have been optimized at the B3LYP/6-311++G(2d,2p) level of density functional theory (DFT). We have found that the molar rotation and the parameters (the helical pitch s and helical radius r) have the direct proportions, in agreement with the formula [M]D = K{(r2s)/(4pi2r2 + s2)}. This provides theoretical predictions for profound study on the helical structure in the future.

Słowa kluczowe

EN

molar rotation; helical structure; helical radius; helical pitch; lactic acid; lactic acid derivatives

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2009
• Tom: Vol. 83, nr 4
• Strony: 641--649
• Opis fizyczny: Bibliogr. 25 poz., rys.

Twórcy

autor

Zhou X. M.

autor

Hou R. Y.

autor

Fu H.

autor

Ma K. S.

autor

Zhou Z. Y.

autor

Zhang A. G.

• College of Chemistry & Chemical Engineering, China University of Petroleum, Shangdong, Dongying, 257061, P. R. China,

Bibliografia

• 1. Lowry T.M, Optical Rotatory Power, Dover Publication: New York, (1964).
• 2. Djerassi C, Optical Rotatory Dispersion: Applications to Organic Chemistry, McGraw-Hill: New York, (1960).
• 3. Biot J.B, Mem. Acad. Sei., 2, 114 (1817).
• 4. Kondru R.K., Wipf P. and Beratan D.N, J. Phys. Chem A, 103, 6603 (1999).
• 5. Polavarapu P.L., Chakraborty D.K. and Ruud K., Chem. Phys. Lett., 319, 595 (2000).
• 6. Grimme S, Bahlmann A. and Haufe G, Chirality, 14, 793 (2002).
• 7. Müller T, Wiberg K.B. and Vaccaro RH., J. Phys. Chem. A, 104, 5959 (2000).
• 8. Coriani S, Pecul M, Rizzo A, Jorgensen P. and Jaszunski M, J. Chem. Phys., 117, 6417 (2002).
• 9. Brewster J.H., J. Am. Chem. Soc., 81, 5475; 5483; 5493 (1959).
• 10. Brewster J.H, Topics in Stereochemistry, Interscience Publishers, New York, 2, 1 (1967).
• 11. Eliel EL. Cf. and Wilen S.H., Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1022, (1994).
• 12. Pecul M., Ruud K, Rizzo A. and Helgaker T, J. Phys. Chem. A, 108, 4269 (2004).
• 13. Pecul M., Chem. Phys. Lett., 418, 1 (2006).
• 14. Zhao S.L., Kong F.Z., Zhou Z.Y, Ma H.K. and Wang W.J, Polish J. Chem., 81, 1807 (2007).
• 15. Zhao S.L., Zhou Z.Y, Wang W.J. and Ma H.K, Int. J. Quant. Chem., 107, 1015 (2007).
• 16. Da Silva CO, Mennucci B. and Vreven T, J. Org. Chem., 69, 8161 (2004).
• 17. Zhou X.M, Zhou Z.Y and Fu H, Polish J. Chem., 79, 1223 (2005).
• 18. Stephens P.J., Devlin F.J, Cheeseman J.R. and Frisch M.J, J. Phys. Chem. A, 105, 5356 (2001).
• 19. Tinoco I. and Freeman M.P., J. Phys. Chem., 61, 1196 (1957).
• 20. Brewster J.H, Tetrahedron, 13, 106(1961).
• 21. Ziffer H, CharneyE. and Weiss U., J. Am. Chem. Soc., 84, 4661 (1962).
• 22. Pecul M.A., Rizzo J. and Leszczyński J, J. Phys. Chem. A, 106, 11008 (2002).
• 23. Barone V, Adamo C. and Lelj F., J. Chem. Phys., 102, 364 (1995).
• 24. Zhou Z.Y, Cheng X.L., Zhou X.M. and Fu H, Chem. Phys. Lett., 353, 281 (2002).
• 25. Frisch M.J, Trucks G.W., Schlegel H.B, Scuseria G.E, Robb M.A, Cheeseman J.R, Montgomery J.A.Jr, Vreven T, Kudin K.N, Burant J.C, Millam J.M, Iyengar S.S., Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, RegaN, Petersson G.A., Nakatsuji H, HadaM, Ehara M, Toyota K., Fukuda R., Hasegawa J, Ishida M., Nakajima T, Honda Y, Kitao O, Nakai H, Kiene M, Li X, Knox J.E, Hratchian H.P, Cross J.B., Adamo C, Jaramillo J, Gomperts R, Stratmann R.E, Yazyev O., Austin A.J, Cammi R, Pomelli C, Ochterski J.W, Ayala P.Y, Morokuma K, Voth G.A., Salvador P, Dannenberg J.J, Zakrzewski V.G., Dapprich S, Daniels A.D., Strain M.C, Farkas O, Malick D.K, Rabuck A.D., Raghavachari K., Foresman J.B, Ortiz J.V, Cui Q, Baboul A.G, Clifford S, Cioslowski J, Stefanov B.B., Liu G, Liashenko A, Piskorz P., Komaromi I, Martin R.L., Fox D.J, Keith T, Al-Laham M.A, Peng C.Y., Nanayakkara A, Challacombe M, Gill P.M.W., Johnson B, Chen W, Wong M.W, Gonzalez C. and Pople J.A, Gaussian OS, revision B.07; Gaussian, Inc. Pittsburgh, PA, (2003).