2-chlorobenzyl methyl selenide | 98369-93-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chlorobenzyl methyl selenide
• 英文别名: Benzene, 1-chloro-2-[(methylseleno)methyl]-；1-chloro-2-(methylselanylmethyl)benzene
• CAS: 98369-93-8
• 化学式: C₈H₉ClSe
• 分子量: 219.572
• InChiKey: ADKSOKHYJXPNMC-UHFFFAOYSA-N

物化性质

• 沸点：
  265.6±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-chlorobenzyl methyl selenide 、 苯甲醛 在 正丁基锂 作用下， 生成 2-(2-氯苯基)-1-苯基乙醇
  参考文献：
  名称：

  由苄基硒化物新型合成苄基锂

  摘要：

  发现苄基硒化物是苄基锂的有价值的前体。公开了新方法的范围。

  DOI：

  10.1016/s0040-4039(00)98521-6
• 作为产物：
  描述：

  2-氯苄溴 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 1.42h， 生成 2-chlorobenzyl methyl selenide
  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

• CLAREMBEAU, M.;KRIEF, A., TETRAHEDRON. LETT., 1985, 26, N 8, 1093-1096
  作者：CLAREMBEAU, M.、KRIEF, A.

  DOI：——

  日期：——
• Novel synthesis of benzyllithiums from benzylselenides
  作者：M. Clarembeau、A. Krief

  DOI：10.1016/s0040-4039(00)98521-6

  日期：1985.1

  Benzylselenides are found to be valuable precursors of benzyllithiums. The scope of the new method is disclosed.

  发现苄基硒化物是苄基锂的有价值的前体。公开了新方法的范围。
• 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.