bis(3-fluoromethyl-2-naphthyl) diselenide | 823178-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: bis(3-fluoromethyl-2-naphthyl) diselenide
• 英文别名: Diselenide, bis[3-(fluoromethyl)-2-naphthalenyl]；2-(fluoromethyl)-3-[[3-(fluoromethyl)naphthalen-2-yl]diselanyl]naphthalene
• CAS: 823178-66-1
• 化学式: C₂₂H₁₆F₂Se₂
• 分子量: 476.286
• InChiKey: PQCUDUGTBXOFSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(3-fluoromethyl-2-naphthyl) diselenide 在 磺酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Experimental and Theoretical Studies on the Nature of Weak Nonbonded Interactions between Divalent Selenium and Halogen Atoms

  摘要：

  To investigate the nature of weak nonbonded selenium(...)halogen interactions ((SeX)-X-... interactions; X = F Cl, and Br), three types of model compounds [2-(CH2X)C6H4SeY (1-3), 3-(CH2X)-2-C10H6-SeY (4-6), and 2-XC6H4CH2SeY (7-9); Y = CN, Cl, Br, SeAr, and Me] were synthesized, and their Se-77 NMR spectroscopic behaviors were analyzed in CDCl3. The gradual upfield shifts of Se-77 NMR absorptions observed for series 1-3 and 4-6 suggested that the strength of (SeX)-X-... interaction decreases in the order of (SeF)-F-... > (SeCl)-Cl-... > (SeBr)-Br-.... The quantum chemical calculations at the B3LYP/631H level using the polarizable continuum model (PCM) revealed that the most stable conformer for 1-3 is the one with an intramolecular short (SeX)-X-... atomic contact in CHCl3 (epsilon = 4.9) and also that the n(x) --> sigma*(se-y) orbital interaction (E-Se...X) can reasonably explain the order of strength for the (SeX)-X-... interactions. On the other hand, the Se-77 NMR absorptions observed for series 7-9 did not shift significantly from the reference compounds (C6H5CH2SeY), indicating the absence of the (SeX)-X-... interaction for 7-9 presumably due to attenuation of basicity for the halogen atom that is substituted directly to the aromatic ring. These observations suggested that the n(x) --> sigma*(se-y) orbital interaction is a dominant factor for formation of weak (SeX)-X-... interactions. Electron correlation was also suggested to be important for the stability.

  DOI：

  10.1021/jo048436a
• 作为产物：
  描述：

  甲基3-氨基-2-萘甲酸酯 在 吡啶 、 盐酸 、 calcium fluoride 、 potassium fluoride 、 lithium aluminium tetrahydride 、 氯化亚砜 、 sodium nitrite 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 88.0h， 生成 bis(3-fluoromethyl-2-naphthyl) diselenide
  参考文献：
  名称：

  Experimental and Theoretical Studies on the Nature of Weak Nonbonded Interactions between Divalent Selenium and Halogen Atoms

  摘要：

  To investigate the nature of weak nonbonded selenium(...)halogen interactions ((SeX)-X-... interactions; X = F Cl, and Br), three types of model compounds [2-(CH2X)C6H4SeY (1-3), 3-(CH2X)-2-C10H6-SeY (4-6), and 2-XC6H4CH2SeY (7-9); Y = CN, Cl, Br, SeAr, and Me] were synthesized, and their Se-77 NMR spectroscopic behaviors were analyzed in CDCl3. The gradual upfield shifts of Se-77 NMR absorptions observed for series 1-3 and 4-6 suggested that the strength of (SeX)-X-... interaction decreases in the order of (SeF)-F-... > (SeCl)-Cl-... > (SeBr)-Br-.... The quantum chemical calculations at the B3LYP/631H level using the polarizable continuum model (PCM) revealed that the most stable conformer for 1-3 is the one with an intramolecular short (SeX)-X-... atomic contact in CHCl3 (epsilon = 4.9) and also that the n(x) --> sigma*(se-y) orbital interaction (E-Se...X) can reasonably explain the order of strength for the (SeX)-X-... interactions. On the other hand, the Se-77 NMR absorptions observed for series 7-9 did not shift significantly from the reference compounds (C6H5CH2SeY), indicating the absence of the (SeX)-X-... interaction for 7-9 presumably due to attenuation of basicity for the halogen atom that is substituted directly to the aromatic ring. These observations suggested that the n(x) --> sigma*(se-y) orbital interaction is a dominant factor for formation of weak (SeX)-X-... interactions. Electron correlation was also suggested to be important for the stability.

  DOI：

  10.1021/jo048436a

文献信息

• Experimental and Theoretical Studies on the Nature of Weak Nonbonded Interactions between Divalent Selenium and Halogen Atoms
  作者：Michio Iwaoka、Takayuki Katsuda、Hiroto Komatsu、Shuji Tomoda

  DOI：10.1021/jo048436a

  日期：2005.1.1

  To investigate the nature of weak nonbonded selenium(...)halogen interactions ((SeX)-X-... interactions; X = F Cl, and Br), three types of model compounds [2-(CH2X)C6H4SeY (1-3), 3-(CH2X)-2-C10H6-SeY (4-6), and 2-XC6H4CH2SeY (7-9); Y = CN, Cl, Br, SeAr, and Me] were synthesized, and their Se-77 NMR spectroscopic behaviors were analyzed in CDCl3. The gradual upfield shifts of Se-77 NMR absorptions observed for series 1-3 and 4-6 suggested that the strength of (SeX)-X-... interaction decreases in the order of (SeF)-F-... > (SeCl)-Cl-... > (SeBr)-Br-.... The quantum chemical calculations at the B3LYP/631H level using the polarizable continuum model (PCM) revealed that the most stable conformer for 1-3 is the one with an intramolecular short (SeX)-X-... atomic contact in CHCl3 (epsilon = 4.9) and also that the n(x) --> sigma*(se-y) orbital interaction (E-Se...X) can reasonably explain the order of strength for the (SeX)-X-... interactions. On the other hand, the Se-77 NMR absorptions observed for series 7-9 did not shift significantly from the reference compounds (C6H5CH2SeY), indicating the absence of the (SeX)-X-... interaction for 7-9 presumably due to attenuation of basicity for the halogen atom that is substituted directly to the aromatic ring. These observations suggested that the n(x) --> sigma*(se-y) orbital interaction is a dominant factor for formation of weak (SeX)-X-... interactions. Electron correlation was also suggested to be important for the stability.