cyclopent-1->3-enyl | 10577-65-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: cyclopent-1->3-enyl
• 英文别名: 2-cyclopenten-1-yl radical；cyclopentenyl radical；2-Cyclopenten-5-yl-Radikal；3-Cyclopentenyl-Radikal；Cyclopentenyl
• CAS: 10577-65-8
• 化学式: C₅H₇
• 分子量: 67.1106
• InChiKey: MNLVCBKWEVXHGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  cyclopent-1->3-enyl 生成 环戊二烯
  参考文献：
  名称：

  Homolytic Bond Dissociation Enthalpies of the C−H Bonds Adjacent to Radical Centers

  摘要：

  Homolytic bond dissociation enthalpies (BDEs) at 0 and 298 K of the C-H bonds adjacent to various radical centers have been obtained from ab initio CBS-4 (complete basis set) model calculations and experimental data available in the literature. The BDEs of the C-H bonds adjacent to the radical centers derived from 11 saturated hydrocarbons were found to be 33.5 +/- 3 kcal/mol at 298 K. The BDEs of the C-H bonds adjacent to nine allylic and benzylic radical centers were found to be 48 +/- 3 kcal/mol at 298 K, but the benzylic C-H BDE of the PhCH2CH2. radical was found to be only 29.7 and 30.5 kcal/mol at 0 and 298 K, respectively. The BDEs of the vinylic C-H bonds adjacent to four vinylic radical centers were found to be 35.5 +/- 3.5 kcal/mol at 298 K. The BDEs of the vinylic C-H bonds adjacent to three allylic radical centers were found to be 56.5 +/- 3 kcal/mol at 298 K. These results suggest that the radical centers weaken the adjacent C-H bond strengths by about 50-70 kcal/mol. The calculated BDEs agree within +/-2 kcal/mol with most of the available experimental results. Isomerization enthalpies of butenes and pentenes have been obtained. Substituent effects on BDEs have also been examined.

  DOI：

  10.1021/jo971768d
• 作为产物：
  描述：

  3,3'-bicyclopentenyl 生成 cyclopent-1->3-enyl
  参考文献：
  名称：

  标记的环戊烯热解过程中的氘-氢交换和加扰反应。根本机制

  摘要：

  DOI：

  10.1021/j100238a019

文献信息

• Roth, Wolfgang R.; Staemmler, Volker; Neumann, Martin, Liebigs Annalen, 1995, # 6, p. 1061 - 1118
  作者：Roth, Wolfgang R.、Staemmler, Volker、Neumann, Martin、Schmuck, Carsten

  DOI：——

  日期：——
• 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.
• Davies, Michael J.; Gilbert, Bruce C., Journal of the Chemical Society. Perkin transactions II, 1984, # 11, p. 1809 - 1816
  作者：Davies, Michael J.、Gilbert, Bruce C.

  DOI：——

  日期：——
• A kinetic study of the reactions of tert-butoxyl with alkenes: hydrogen abstraction vs. addition
  作者：P. C. Wong、D. Griller、J. C. Scaiano

  DOI：10.1021/ja00383a018

  日期：1982.9
• Homolytic Bond Dissociation Enthalpies of the C−H Bonds Adjacent to Radical Centers
  作者：Xian-Man Zhang

  DOI：10.1021/jo971768d

  日期：1998.3.1

  Homolytic bond dissociation enthalpies (BDEs) at 0 and 298 K of the C-H bonds adjacent to various radical centers have been obtained from ab initio CBS-4 (complete basis set) model calculations and experimental data available in the literature. The BDEs of the C-H bonds adjacent to the radical centers derived from 11 saturated hydrocarbons were found to be 33.5 +/- 3 kcal/mol at 298 K. The BDEs of the C-H bonds adjacent to nine allylic and benzylic radical centers were found to be 48 +/- 3 kcal/mol at 298 K, but the benzylic C-H BDE of the PhCH2CH2. radical was found to be only 29.7 and 30.5 kcal/mol at 0 and 298 K, respectively. The BDEs of the vinylic C-H bonds adjacent to four vinylic radical centers were found to be 35.5 +/- 3.5 kcal/mol at 298 K. The BDEs of the vinylic C-H bonds adjacent to three allylic radical centers were found to be 56.5 +/- 3 kcal/mol at 298 K. These results suggest that the radical centers weaken the adjacent C-H bond strengths by about 50-70 kcal/mol. The calculated BDEs agree within +/-2 kcal/mol with most of the available experimental results. Isomerization enthalpies of butenes and pentenes have been obtained. Substituent effects on BDEs have also been examined.