1-茚基 | 79317-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 中文名称: 1-茚基
• 英文名称: 1-indenyl
• 英文别名: 1-Ind；indenyl；indenyl radical；1H-inden-1-yl
• CAS: 79317-94-5
• 化学式: C₉H₇
• 分子量: 115.155
• InChiKey: MGHNDJJPPOAIHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• 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：

  1-bromoindene 生成 1-茚基
  参考文献：
  名称：

  Photoionization of Three Isomers of the C₉H₇ Radical

  摘要：

  Three resonance-stabilized radicals, 1-indenyl (Ind), 1-phenylpropargyl (1PPR), and 3-phenylpropargyl (3PPR), all isomers of the composition C9H7, were generated by jet flash pyrolysis. Their photoionization was examined by VUV synchrotron radiation. The mass spectra show a clean and efficient radical generation when the pyrolysis is turned on. To study the photoionization, photoion yield measurements and threshold photoionization spectroscopy techniques were applied. We determined adiabatic ionization energies (IEad) of 7.53 eV for Ind, 7.20 eV for 3PPR, and 7.4 eV for 1PPR. Ab initio calculations show no major change in geometry upon ionization, in agreement with ionization from a nonbonding molecular orbital. The IEs were also computed and are in agreement with the measured ones. The difference in the IE might allow a distinction of the three isomers in flames. In the indenyl spectrum, an excited a(+) B-3(2) state of the cation was identified at 8.10 eV, which shows a low-energy vibrational progression of 61 meV. Furthermore, we have examined the dissociative photoionization of the precursors. The indenyl precursor, 1-indenyl bromide, undergoes dissociative photoionization to Ind(+). An appearance energy (AE(0K)) of 10.2 eV was obtained from fitting the experimental breakdown diagram. A binding energy of 1.8 eV can thus be determined for the C-Br bond in 1-indenyl bromide. The phenylpropargyl precursors 1PPBr (1-phenylpropargyl bromide/3-phenyl-3-bromopropyne) and 3PPBr (3-phenylpropargyl bromide/1-phenyl-3-bromopropyne) also lose a bromine atom upon dissociative photoionization. Approximate appearance energies of 9.8 eV for 3PPBr and 9.3 eV for 1PPBr have been determined.

  DOI：

  10.1021/jp9068569

文献信息

• Stabilities of highly conjugated radicals from bond homolysis rates
  作者：David A. Robaugh、Stephen E. Stein

  DOI：10.1021/ja00272a011

  日期：1986.6

  On mesure les vitesses d'homolyse de la liaison benzyle C-CH 3 des ethyl-4 styrene, phenyl-1butene-1, diphenyl-1,1 ethane, diphenyl-2,2 propane et methyl-1 indene dans un appareil de pyrolyse a tres basse pression

  On mesure les vitesses d'homolyse de la liaison benzle C-CH 3 desethyl-4 苯乙烯, phenyl-1butene-1, diphenyl-1,1 乙烷, diphenyl-2,2 propane etmethyl-1 indene dans un appareil de hotlyse三重低音压力
• Rate Constants for Termination and TEMPO Trapping of Some Resonance Stabilized Hydroaromatic Radicals in the Liquid Phase
  作者：I. W. C. E. Arends、P. Mulder、K. B. Clark、D. D. M. Wayner

  DOI：10.1021/j100020a047

  日期：1995.5

  The rate constants for the termination reaction (2k(1)) of some resonance stabilized carbon centered radicals (SR(.)) derived from hydroaromatics (SR(.) + SR(.) --> P) have been determined at 294 +/- 2 K by laser flash photolysis with UV-vis detection. The radicals were generated by hydrogen atom abstraction by t-BuO(.) radicals from the corresponding hydrocarbon (SRH + t-BuO(.) --> SR(.) + t-BuOH, k(4)). The extinction coefficients (epsilon) Of the SR(.), essential to calculate 2k(1), were obtained using a relative kinetic technique. The change in 2k(1) for the radicals derived from 1,4-cyclohexadiene, fluorene, 9,10-dihydroanthracene, diphenylmethane, tetralin, indan, indene, and phenol appeared to be modest; a range of 2k(1) = 2-10 x 10(9) M(-1) s(-1) in mixtures of benzene and di-tert-butyl peroxide was observed. Most of the rate constants are near the diffusion controlled limit. In contrast, quenching the radicals with a persistent radical, 2,2,5,5-tetramethylpiperidin-1-oxyl (TEMPO), resulted in a larger variation of <0.01-23 x 10(7) M(-1) s(-1). The strength of the N-O bond formed in the latter process may have an important contribution to the observed rate constant.
• Unimolecular dissociation of cyclopentadiene and indene
  作者：Whikun Yi、Arun Chattopadhyay、Richard Bersohn

  DOI：10.1063/1.460433

  日期：1991.5

  The dissociation of hydrogen atoms from the methylene group of cyclopentadiene (CP) and indene (ID) excited with a 193 nm photon has been studied by hydrogen atom laser induced fluorescence. The rate of dissociation of IND was 7.4×106 s−1 but that of CP was too fast to measure. The ratio of H atoms to D atoms generated from 5-deuteriocyclopentadiene (5-dCP) was 3.91±0.46. Rice–Ramsberger–Kassel–Marcus theory was used to calculate the rates of dissociation of CP and 5-dCP. The quantum yield for dissociating H atoms from CP was 0.85±0.07. The ejected H atoms have a Maxwell velocity distribution with temperatures which are equal to the vibrational temperatures, 3690 and 2479 K for CP and IND, respectively. The most important result of the work is this confirmation of an earlier finding on a different set of molecules that the translational temperature of the fragments after the dissociation is equal to the vibrational temperature before the dissociation. This is explained by the assumption that the motion of the fast, light hydrogen atom is partly decoupled from that of the heavier, slower atoms.
• Photoionization of Three Isomers of the C₉H₇ Radical
  作者：Patrick Hemberger、Michael Steinbauer、Michael Schneider、Ingo Fischer、Melanie Johnson、Andras Bodi、Thomas Gerber

  DOI：10.1021/jp9068569

  日期：2010.4.15

  Three resonance-stabilized radicals, 1-indenyl (Ind), 1-phenylpropargyl (1PPR), and 3-phenylpropargyl (3PPR), all isomers of the composition C9H7, were generated by jet flash pyrolysis. Their photoionization was examined by VUV synchrotron radiation. The mass spectra show a clean and efficient radical generation when the pyrolysis is turned on. To study the photoionization, photoion yield measurements and threshold photoionization spectroscopy techniques were applied. We determined adiabatic ionization energies (IEad) of 7.53 eV for Ind, 7.20 eV for 3PPR, and 7.4 eV for 1PPR. Ab initio calculations show no major change in geometry upon ionization, in agreement with ionization from a nonbonding molecular orbital. The IEs were also computed and are in agreement with the measured ones. The difference in the IE might allow a distinction of the three isomers in flames. In the indenyl spectrum, an excited a(+) B-3(2) state of the cation was identified at 8.10 eV, which shows a low-energy vibrational progression of 61 meV. Furthermore, we have examined the dissociative photoionization of the precursors. The indenyl precursor, 1-indenyl bromide, undergoes dissociative photoionization to Ind(+). An appearance energy (AE(0K)) of 10.2 eV was obtained from fitting the experimental breakdown diagram. A binding energy of 1.8 eV can thus be determined for the C-Br bond in 1-indenyl bromide. The phenylpropargyl precursors 1PPBr (1-phenylpropargyl bromide/3-phenyl-3-bromopropyne) and 3PPBr (3-phenylpropargyl bromide/1-phenyl-3-bromopropyne) also lose a bromine atom upon dissociative photoionization. Approximate appearance energies of 9.8 eV for 3PPBr and 9.3 eV for 1PPBr have been determined.