INTERACTION BETWEEN STACKED ARYL GROUPS IN 1,8-DIARYLNAPHTHALENES - DOMINANCE OF POLAR/PI OVER CHARGE-TRANSFER EFFECTS

被引:216
作者
COZZI, F [1 ]
SIEGEL, JS [1 ]
机构
[1] UNIV CALIF SAN DIEGO,DEPT CHEM,LA JOLLA,CA 92093
关键词
D O I
10.1351/pac199567050683
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several 1,8-diarylnaphthalenes have been prepared, and the barrier to rotation around the aryl/naphthalene bond has been measured. In these molecules steric congestion forces the aryls in a parallel stacked geometry. The barriers to rotation were used to evaluate the strength and to investigate the nature of the interaction between the arenes. The variance of the Delta G(not equal) for the rotation upon arene substitution with electron donating or electron withdrawing groups indicates that polar/pi electrostatic effects dominate over charge-transfer effects in determining the arene/arene interaction.
引用
收藏
页码:683 / 689
页数:7
相关论文
共 28 条
  • [1] Hunter C.A., Sanders J.K.M., J. Am. Chem. Soc., 112, (1990)
  • [2] Trost B.M., O' Krongly D., Belletire J.L., Belletire, J. Am. Chem. Soc., 102, (1980)
  • [3] Benzing T., Tjivikua T., Wolfe J., J. Rebek Science, 242, (1988)
  • [4] Saenger W., Principles of Nucleic Acid Structures, p, 132, (1984)
  • [5] Claessens M., Palombini L., Stein M.-L., J. Reisse New J. Chem., 6, (1982)
  • [6] Cox E., Cruickshank D.W.J., Smith J.A.C., Proc. R. Soc. London, A, A247, (1958)
  • [7] Lowden L.J., Chandler D.J., J. Chem. Phys., 61, (1974)
  • [8] Shi X., Bartell L.S., J. Chem. Phys., 92, (1988)
  • [9] House H.O., Koepsell D.G., Campbell W.J., J. Org. Chem., 37, (1972)
  • [10] House H.O., Campbell W.J., Gall M., J. Org. Chem., 35, (1970)