物理化学学报 >> 1991, Vol. 7 >> Issue (02): 191-195.doi: 10.3866/PKU.WHXB19910212

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乙酰丙酮和1-萘甲酸甲酯加成物C17H18O4的晶体结构和分子力学计算

胡盛志; 陈明旦; 刘晓云; 周原朗   

  1. 厦门大学化学系，厦门 361005；加拿大Simon Fraser大学化学系
  • 收稿日期:1989-10-04 修回日期:1990-03-10 发布日期:1991-04-15
  • 通讯作者: 胡盛志

Crystal Structure and Molecular Mechanics Calculations of the Addition Product of Acetylacetone and Methyl 1-Naphthoate, C17H18O4

Hu Sheng-Zhi; Chen Ming-Dan; Liu Xiao-Yun; Zhou Yuan-Lang   

  1. Department of Chemistry, Xiamen University, Xiamen 361005; Department of Chemistry, Simon Fraser University, Burnuby, B.C.Canada
  • Received:1989-10-04 Revised:1990-03-10 Published:1991-04-15
  • Contact: Hu Sheng-Zhi

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关键词: 乙酰丙酮, 1-萘甲酸甲酯, 加成物, 晶体结构和分子力学计算

Abstract: The structure of the product from the [2+2] photocycloaddition of acetylacetone to methyl 1-naphthoate was determined by X-ray crystallography. Crystal data. C_(17)H_(18)O_4, triclinic, P_1~-, a=0.7401(1), b=0.7656(1), c=1.3882(1) nm, α=84.75(1), β=86.49(1), γ=65.08(1)°, V=0.7102 nm, Z=2, D_c=1.339 g·cm~(-3), μ(MoK_a)=1.0 cm~(-1), F(000)=304. The structure was solved by direct methods and refined to final R=0.049 for 2442 MoKa reflections. The particular bridged structure of the product molecule indicates a [2+2+2] intramolecular cycloaddition in succession to the primary [2+2] photocycloaddition. Molecular mechanics calculations confirmed further that the molecular structure of the ultimate product takes a configuration of comparatively favourable steric energy even though the bridged structure itself is rather strained.

Key words: Acetylacetone, Metyl 1-naphthoate, Addition product, Crystal structure and molecular mechaniec calculation