dibromomethyl | 14362-13-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: dibromomethyl
• 英文别名: Dibromomethyl radical
• CAS: 14362-13-1
• 化学式: CHBr₂
• 分子量: 172.827
• InChiKey: HFPGRVHMFSJMOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  3
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  二溴甲烷 在 氯 作用下， 生成 dibromomethyl
  参考文献：
  名称：

  单取代和双取代的氟甲烷，氯甲烷和溴甲烷的光氯化动力学

  摘要：

  DOI：

  10.1021/j100317a023

文献信息

• Matrix‐Isolation Studies of the Infrared Spectra of the Free Radicals CCl₃ and CBr₃
  作者：Ernest E. Rogers、Stanley Abramowitz、Marilyn E. Jacox、Dolphus E. Milligan

  DOI：10.1063/1.1673285

  日期：1970.3

  CCl3 has been stabilized both by the reaction of lithium atoms with CCl4 in an argon matrix at 20°K and by the vacuum-ultraviolet photolysis of HCCl3 or of DCCl3 in an argon or a nitrogen matrix at 14°K. The analogous techniques have been found to lead to the stabilization of CBr3. The product spectra obtained in the lithium-atom experiments are considerably simpler than those obtained in the previous studies of the reaction of lithium atoms with matrix-isolated CX4. In the vacuum-ultraviolet photolysis experiments, DCCl2, HCBr2, and CBr2 have also been observed. The absorption frequencies and contours obtained for ν3 of CCl3 and of CBr3 are independent of the method used to produce these species, suggesting that lithium atoms and their reaction products do not appreciably perturb the degenerate stretching mode of either CCl3 or CBr3. Despite yields of these species comparable to those previously reported, absorptions at 674 and at 582 cm−1, previously attributed to ν1 of CCl3 and CBr3, respectively, are completely missing from the present experiments. No other absorption attributable to ν1 of either species has been detected. It is concluded that a pyramidal (C3υ) structure for CCl3 and for CBr3 has not been established.
• Matrix Infrared Spectrum and Bonding in the Dibromomethyl Radical
  作者：T. Granville Carver、Lester Andrews

  DOI：10.1063/1.1670887

  日期：1969.5.15

  Simultaneous condensation of bromoform and lithium atoms at high dilution in argon on a CsI window at 15°K produces new infrared absorptions which are assigned to lithium bromide and the dibromomethyl radical. The identity of dibromomethyl is confirmed by comparison of spectra obtained from HCBr3, DCBr3, and HCBr2Cl precursors reacting with lithium and sodium. These new absorptions are assigned to the antisymmetric H–C–Br bending and C–Br stretching modes and the symmetric C–Br vibration. The antisymmetric vibrational assignments are supported by product-rule and normal-coordinate calculations which give the potential constants F55 = 3.10 ± 0.10 mdyn/Å, F56 = 0.32 ± 0.01 mdyn/rad, and F66 = 0.50 ± 0.05 mdyn·Å/rad2, while the symmetric C–Br mode yields an approximate force constant F22 = 3.7 ± 0.4 mdyn/Å. The C–Br valence force constants for bromomethyl radicals exceed normal C–Br values, while electronic stabilization for these radicals is indicated by bond dissociation energies. Similar results for chloromethyl radicals, in contrast to fluoromethyl radicals, suggest that (p–d)π bonding between the free-radical carbon orbital and the d orbitals on chlorine and bromine might account for the stabilization of chloromethyl and bromomethyl radicals, which cannot occur for fluoromethyl radicals or molecules with completely satisfied valence.
• Atmospheric chemistry of CH2BR2: Rate coefficients for its reaction with Cl atoms and OH and the chemistry of the CHBr2O radical
  作者：John J. Orlando、Geoffrey S. Tyndall、Timothy J. Wallington、Marchoe Dill

  DOI：10.1002/(sici)1097-4601(1996)28:6<433::aid-kin5>3.0.co;2-w

  日期：——
• Absolute Rate Constants for the Reactions of Cl Atoms with CH₃Br, CH₂Br₂, and CHBr₃
  作者：Kyriakos G. Kambanis、Yannis G. Lazarou、Panos Papagiannakopoulos

  DOI：10.1021/jp9719671

  日期：1997.11.1

  The rate constants for the reactions of chlorine atoms with the complete series of the three bromomethanes CH3Br (1), CH2Br2 (2), and CHBr3 (3) were measured in a very low pressure reactor, employing a microwave discharge for the generation of Cl atoms with mass spectrometric detection of reactants and products. The experiments were performed in the temperature range 273-363 K and at total pressures similar to 1 mTorr. The reactions proceed via hydrogen atom transfer leading to HCl product and the corresponding bromomethyl radicals. Their rate constant expressions are (in cm(3) molecule(-1) s(-1)): k(l) = (1.66 +/- 0.14) x 10(-11) exp(-1072 +/- 46/T), k(2) = (0.84 +/- 0.15) x 10(-11) exp(-911 +/- 101/T), and k(3) = (0.43 +/- 0.11) x 10(-11) exp(-809 +/- 142/T). The activation energy of the reaction decreases with additional bromine substitution, which is attributed to the gradual weakening of the corresponding C-H bond strength. Ab initio theoretical calculations performed at the MP2/6-31++G(2d,2p) level of theory suggest C-H bond strengths for CH3Br, CH2Br2, and CHBr3 of 416.58, 407.03, and 396.60 kJ mol(-1), respectively.
• Studies in electron impact methods. Part 6.—The formation of the methine and carbon ions
  作者：Rowland I. Reed、Walter Snedden

  DOI：10.1039/tf9595500876

  日期：——