8-(methyl)-1-(p-anisylselanyl)naphthalene | 1210856-98-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-(methyl)-1-(p-anisylselanyl)naphthalene
• 英文别名: 1-(4-Methoxyphenyl)selanyl-8-methylnaphthalene；1-(4-methoxyphenyl)selanyl-8-methylnaphthalene
• CAS: 1210856-98-6
• 化学式: C₁₈H₁₆OSe
• 分子量: 327.284
• InChiKey: QMJGYRHZAGZBMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  、 bis(4-methoxyphenyl)diselenide 以 乙醚 为溶剂， 以88%的产率得到8-(methyl)-1-(p-anisylselanyl)naphthalene
  参考文献：
  名称：

  H/D Isotope Effect on ⁷⁷Se NMR Chemical Shifts in 8-Methyl-1-(arylselanyl)naphthalenes and Related Selenides: Nonbonded C─H—Se Through-Space Versus Through-Bond Mechanisms

  摘要：

  Se-77 NMR chemical shifts of methyl-d(3) derivatives of 8-methyl-1-(phenylselanyl)naphthalene (1) and 8-methyl-1-(p-anisylselanyl)naphthalene (2) are observed 0.25 and 0.20 ppm upfield from 1 and 2, respectively. The observations must be the reflection of the nonbonded interactions of the C-H-Se 3c-4e type in 1 and 2. The mechanism is elucidated by means of crystallographic and theoretical investigations. The nonbonded distance between Se and C-Me (2.989 angstrom) is observed to be shorter than the sum of the van der Waals radii of the two by 0.91 angstrom in 2. 1 and 2 may be in equilibrium between conformers A and B in solution, where Se-C-i is perpendicular to the naphthyl plane in A and it is on the plane in B. Natural bond orbital (NBO) analysis on 1 revealed that the nonbonded n(p)(Se)-sigma *(C-H) interaction contributes in A, whereas nonbonded n(s)(Se)-sigma *(C-H) and double sigma (C-H)-sigma *(Se-C) interactions operate in B.

  DOI：

  10.1080/10426500902947807

文献信息

• H/D Isotope Effect on ⁷⁷Se NMR Chemical Shifts in 8-Methyl-1-(arylselanyl)naphthalenes and Related Selenides: Nonbonded C─H—Se Through-Space Versus Through-Bond Mechanisms
  作者：Satoko Hayashi、Kentaro Yamane、Waro Nakanishi

  DOI：10.1080/10426500902947807

  日期：2009.6.23

  Se-77 NMR chemical shifts of methyl-d(3) derivatives of 8-methyl-1-(phenylselanyl)naphthalene (1) and 8-methyl-1-(p-anisylselanyl)naphthalene (2) are observed 0.25 and 0.20 ppm upfield from 1 and 2, respectively. The observations must be the reflection of the nonbonded interactions of the C-H-Se 3c-4e type in 1 and 2. The mechanism is elucidated by means of crystallographic and theoretical investigations. The nonbonded distance between Se and C-Me (2.989 angstrom) is observed to be shorter than the sum of the van der Waals radii of the two by 0.91 angstrom in 2. 1 and 2 may be in equilibrium between conformers A and B in solution, where Se-C-i is perpendicular to the naphthyl plane in A and it is on the plane in B. Natural bond orbital (NBO) analysis on 1 revealed that the nonbonded n(p)(Se)-sigma *(C-H) interaction contributes in A, whereas nonbonded n(s)(Se)-sigma *(C-H) and double sigma (C-H)-sigma *(Se-C) interactions operate in B.