(2-bromophenyl)methaneselenenyl cyanide | 57239-50-6

• 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-bromophenyl)methaneselenenyl cyanide
• 英文别名: 1-bromo-2-(selenocyanatomethyl)benzene；2-bromobenzyl selenocyanate；2-Brombenzylselenocyanat；(2-Bromophenyl)methyl selenocyanate
• CAS: 57239-50-6
• 化学式: C₈H₆BrNSe
• 分子量: 275.006
• InChiKey: BSDKDQJAMNCZGA-UHFFFAOYSA-N

物化性质

• 沸点：
  334.6±44.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-bromophenyl)methaneselenenyl cyanide 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 bis(2-bromobenzyl) 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
• 作为产物：
  描述：

  potassium selenocyanate 、 2-溴溴苄 以 乙醇 为溶剂， 反应 0.17h， 以100%的产率得到(2-bromophenyl)methaneselenenyl cyanide
  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

• Efficient synthesis of novel chalcogen-containing derivatives of DNA nucleobases
  作者：Guoxiong Hua、Junyi Du、David B. Cordes、Alexandra M.Z. Slawin、J. Derek Woollins

  DOI：10.1016/j.tet.2015.02.005

  日期：2015.3

  The formation of a library of chalcogen-containing DNA nucleobase derivatives is presented. Reacting easily accessible 9-(2-bromoethyl)adenine with chalcogen-containing nucleophilic reagents led to a series of novel heteroatom derivatives incorporating S, Se and Te atoms in satisfactory yields. Two representative X-ray structures are reported. (C) 2015 Elsevier Ltd. All rights reserved.