4,4'-dibromothiobenzophenone | 36240-98-9

• 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: 4,4'-dibromothiobenzophenone
• 英文别名: p,p'-Dibrom-thiobenzophenon；4,4'-Dibrom-thiobenzophenon；Bis(4-bromophenyl)methanethione
• CAS: 36240-98-9
• 化学式: C₁₃H₈Br₂S
• 分子量: 356.081
• InChiKey: SZPARWFZYZSQEP-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C
• 沸点：
  393.2±52.0 °C(Predicted)
• 密度：
  1.713±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4'-dibromothiobenzophenone 在 silver(II) oxide 、 叔丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 78.0h， 生成
  参考文献：
  名称：

  Structure−Property Relationships in Trimethylenemethane-Type Biradicals. 2. Synthesis and EPR Spectral Characterization of Dinitroxide Biradicals

  摘要：

  Several trimethylenemethane-type (TMM-type) dinitroxide biradicals have been prepared that differ in tert-butylaminoxylphenyl ring torsion angles by virtue of different steric demands of their "spin-protecting groups". In addition, the synthesis of a TMM-type dinitroxide having a planar pi-system is reported. The synthetic route employed for the planar TMM-type biradical is general and should therefore expand, the utility of TMM-type biradicals that are susceptible to bond torsions that attenuate exchange coupling. The compounds presented are designed to be effective to map out J-coupling/conformation space in TMM-type biradicals. EPR spectroscopic parameters (hfcc and D-values) were compared to determine if their values reflected differences in conformation in the series of biradicals. Interestingly, neither N- nor H-hfcc varied within our series of biradicals/monoradicals in a regular fashion, indicating that there is no apparent relationship between N- or H-hfcc and conformation (as judged by molecular mechanics calculations). However, D-values, estimated from relative intensities of Delta m(s) = 1 and Delta m(s) = 2 transitions, are consistent with a varied degree of delocalization in the dinitroxides: smaller D-values for biradicals having smaller aryl torsions (and greater delocalization), and larger D-values for dinitroxides having greater aryl torsions (and less delocalization). All the biradicals studied, except 5(..), exhibited linear Curie plots. The linear Curie plots are consistent with both triplet ground-states and singlet-triplet degeneracies. Interestingly, dinitroxide 6(..) exhibited a linear Curie plot, despite the lack of a pi-coupling fragment. Biradical 5(..), however, is a ground-state singlet; species with the triplet lying about 140 cal/mol above the singlet.

  DOI：

  10.1021/jo990061j
• 作为产物：
  描述：

  4,4'-二溴二苯甲酮 在 tetraphosphorus decasulfide 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 4,4'-dibromothiobenzophenone
  参考文献：
  名称：

  Structure−Property Relationships in Trimethylenemethane-Type Biradicals. 2. Synthesis and EPR Spectral Characterization of Dinitroxide Biradicals

  摘要：

  Several trimethylenemethane-type (TMM-type) dinitroxide biradicals have been prepared that differ in tert-butylaminoxylphenyl ring torsion angles by virtue of different steric demands of their "spin-protecting groups". In addition, the synthesis of a TMM-type dinitroxide having a planar pi-system is reported. The synthetic route employed for the planar TMM-type biradical is general and should therefore expand, the utility of TMM-type biradicals that are susceptible to bond torsions that attenuate exchange coupling. The compounds presented are designed to be effective to map out J-coupling/conformation space in TMM-type biradicals. EPR spectroscopic parameters (hfcc and D-values) were compared to determine if their values reflected differences in conformation in the series of biradicals. Interestingly, neither N- nor H-hfcc varied within our series of biradicals/monoradicals in a regular fashion, indicating that there is no apparent relationship between N- or H-hfcc and conformation (as judged by molecular mechanics calculations). However, D-values, estimated from relative intensities of Delta m(s) = 1 and Delta m(s) = 2 transitions, are consistent with a varied degree of delocalization in the dinitroxides: smaller D-values for biradicals having smaller aryl torsions (and greater delocalization), and larger D-values for dinitroxides having greater aryl torsions (and less delocalization). All the biradicals studied, except 5(..), exhibited linear Curie plots. The linear Curie plots are consistent with both triplet ground-states and singlet-triplet degeneracies. Interestingly, dinitroxide 6(..) exhibited a linear Curie plot, despite the lack of a pi-coupling fragment. Biradical 5(..), however, is a ground-state singlet; species with the triplet lying about 140 cal/mol above the singlet.

  DOI：

  10.1021/jo990061j

文献信息

• Reactions of Alkylidenetriphenylphosphoranes with Sulfur
  作者：Hirokazu Tokunaga、Kin-ya Akiba、Naoki Inamoto

  DOI：10.1246/bcsj.45.506

  日期：1972.2

  Reaction of diarylmethylenetriphenylphosphoranes with sulfur gave thiobenzophenones and triphenylphosphine sulfide in good yields. Reaction of benzylidenetriphenylphosphoranes with sulfur gave triphenylphosphine sulfide and 5,7-diphenyl-l,2,3,4,6-pentathiepane. More active alkylidenetriphenylphosphoranes such as isopropylidene- or sec-butylidenetriphenylphosphorane gave the corresponding phosphonium

  二芳基亚甲基三苯基膦与硫的反应以良好的产率得到噻吩二苯酮和硫化三苯基膦。亚苄基三苯基膦与硫的反应得到三苯基硫化膦和 5,7-二苯基-1,2,3,4,6-五硫杂环庚烷。更活泼的亚烷基三苯基正膦如异丙叉或仲亚丁基三苯基正膦产生相应的含硫原子的鏻甜菜碱或通过甜菜碱的空气氧化和水解产生的鏻盐。α-苯甲酰基苄叉三苯基正膦不与硫反应。简要讨论了亚烷基正膦对硫的反应性。
• A Convenient Preparation of Sulfines (R₂CSO) from Thioketones
  作者：Ruili Huang、James H. Espenson

  DOI：10.1021/jo990967p

  日期：1999.9.1
• Development of novel proton-conductive polymers for proton exchange membrane fuel cell (PEMFC) technology
  申请人：Bae Chulsung

  公开号：US20070048579A1

  公开（公告）日：2007-03-01

  New thermally and chemically stable sulfonic acid-containing polymers are synthesized via post-sulfonation of aromatic polymers. These new polymers provide unique benefits to proton exchange membrane fuel cell technology (“PEMFC”). As a sulfonic acid moiety can be easily installed into an aromatic ring via electrophilic sulfonation, even in the presence of an electron-withdrawing substituent such as —F, rigid polymers consisting of aromatic rings at either the side chain or main chain can be prepared with a wide range of substituents and flexibility in properties. Novel synthetic procedures are provided for synthesis of the polymers.
• US7615300B2
  申请人：——

  公开号：US7615300B2

  公开（公告）日：2009-11-10
• Structure−Property Relationships in Trimethylenemethane-Type Biradicals. 2. Synthesis and EPR Spectral Characterization of Dinitroxide Biradicals
  作者：David A. Shultz、Andrew K. Boal、Hyoyoung Lee、Gary T. Farmer

  DOI：10.1021/jo990061j

  日期：1999.6.1

  Several trimethylenemethane-type (TMM-type) dinitroxide biradicals have been prepared that differ in tert-butylaminoxylphenyl ring torsion angles by virtue of different steric demands of their "spin-protecting groups". In addition, the synthesis of a TMM-type dinitroxide having a planar pi-system is reported. The synthetic route employed for the planar TMM-type biradical is general and should therefore expand, the utility of TMM-type biradicals that are susceptible to bond torsions that attenuate exchange coupling. The compounds presented are designed to be effective to map out J-coupling/conformation space in TMM-type biradicals. EPR spectroscopic parameters (hfcc and D-values) were compared to determine if their values reflected differences in conformation in the series of biradicals. Interestingly, neither N- nor H-hfcc varied within our series of biradicals/monoradicals in a regular fashion, indicating that there is no apparent relationship between N- or H-hfcc and conformation (as judged by molecular mechanics calculations). However, D-values, estimated from relative intensities of Delta m(s) = 1 and Delta m(s) = 2 transitions, are consistent with a varied degree of delocalization in the dinitroxides: smaller D-values for biradicals having smaller aryl torsions (and greater delocalization), and larger D-values for dinitroxides having greater aryl torsions (and less delocalization). All the biradicals studied, except 5(..), exhibited linear Curie plots. The linear Curie plots are consistent with both triplet ground-states and singlet-triplet degeneracies. Interestingly, dinitroxide 6(..) exhibited a linear Curie plot, despite the lack of a pi-coupling fragment. Biradical 5(..), however, is a ground-state singlet; species with the triplet lying about 140 cal/mol above the singlet.