thioacetic acid S-(10-iododecyl) ester | 193081-88-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: thioacetic acid S-(10-iododecyl) ester
• 英文别名: 1-acetylthio-10-iododecane；S-(10-iododecyl) ethanethioate
• CAS: 193081-88-8
• 化学式: C₁₂H₂₃IOS
• 分子量: 342.285
• InChiKey: CNTTTWDBRWFORV-UHFFFAOYSA-N

物化性质

• 沸点：
  360.6±15.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  thioacetic acid S-(10-iododecyl) ester 在 盐酸 作用下， 以 甲醇 、 异丙醇 为溶剂， 生成 10-(4-methyl-1,3-thiazol-3-ium-3-yl)decane-1-thiol;chloride
  参考文献：
  名称：

  Multistep Synthesis on the Surface of Self-Assembled Thiolate Monolayers on Gold:  Probing the Mechanism of the Thiazolium-Promoted Acyloin Condensation

  摘要：

  DOI：

  10.1021/ja970627q
• 作为产物：
  描述：

  S-[10-(4-methylphenyl)sulfonyloxydecyl] ethanethioate 在 sodium iodide 作用下， 以 异丙醇 为溶剂， 生成 thioacetic acid S-(10-iododecyl) ester
  参考文献：
  名称：

  Multistep Synthesis on the Surface of Self-Assembled Thiolate Monolayers on Gold:  Probing the Mechanism of the Thiazolium-Promoted Acyloin Condensation

  摘要：

  DOI：

  10.1021/ja970627q

文献信息

• Au-S-CnH2n-Q3CNQ: self-assembled monolayers for molecular rectification
  作者：Geoffrey J. Ashwell、Anna Chwialkowska、L. R. Hermann High

  DOI：10.1039/b403942d

  日期：——

  Self-assembled monolayers (SAMs) formed from Z-β-[N-(ω-acetylthioalkyl)-4-quinolinium]-α-cyano-4-styryldicyanomethanide (1) on gold-coated highly oriented pyrolytic graphite exhibit asymmetric current–voltage characteristics that are independent of the length of the linking group [Au-S-CnH2n-Q3CNQ where 3 ≤ n ≤ 12]. The contribution to the electrical asymmetry arising from the chromophore being asymmetrically located between the electrodes is negligible compared to that induced by the non-planar donor–(π-bridge)–acceptor moiety. Current rectification ratios of 30 at ±1 V are typical (cf. 8 for C16H33-Q3CNQ Langmuir–Blodgett films) but also fall within the range 10 to 80 at ±1 V. Molecular dimensions within the film are consistent with the D–π–A chromophores being upright and closely packed: the thickness increases with the length of the linking CnH2n group and areas of 0.33 ± 0.03 nm2 molecule−1 approximate to the van der Waals cross-section of the chromophore.

  在金涂层高取向热解石墨上形成的、由Z-β-[N-(ω-乙酰硫代烷基)-4-喹啉季]-α-氰基-4-苯乙烯基二氰亚甲基（1）组成之自组装单层膜，展现出了与连接基团长度无关的非对称电流-电压特性[Au-S-CnH2n-Q3CNQ，其中3 ≤ n ≤ 12]。相比于由非平面给体-(π桥)-受体部分诱导的电性不对称，发色团非对称地位于电极间所产生的电性不对称贡献可以忽略不计。典型情况下，在±1 V的电压下，电流整流比为30（对比C16H33-Q3CNQ朗缪尔-布洛杰特膜的8），但在±1 V下也落在10到80的范围内。膜内分子尺寸与D-π-A发色团直立且紧密排列的情况一致：厚度随着连接CnH2n基团的长度增加而增加，而每分子0.33 ± 0.03 nm²的面积接近于发色团的范德华横截面。
• Merocyanine dyes: self-assembled monolayers
  作者：Geoffrey J. Ashwell、Gary A. N. Paxton、Anne J. Whittam、Wayne D. Tyrrel、Martial Berry、Dejian Zhou

  DOI：10.1039/b110676g

  日期：2002.5.22

  4-2-[N-(10-Thiodecyl)quinolinium-4-yl]vinyl}phenolate self-assembles on gold with a contact area of 0.35 ± 0.03 nm2 molecule−1, monolayer thickness of 1.64 ± 0.07 nm, and dielectric permittivity components of εr ≈ 2.8 and εi ≈ 0.6 at 632.8 nm, which are reduced to ca. 2.0 and 0 respectively when exposed to an acidic medium. The films undergo a change from purple (merocyanine form) to yellow (protonated form) and, by monitoring changes in the reflectance, may be used as sensors with a detection limit of <1 ppm for NH3 in a carrier gas. Langmuir–Blodgett (LB) films of the N-octadecyl analogue show similar behaviour but, for sensing applications, are disadvantaged because the phenolate group is adjacent to the substrate. They have a contact area and monolayer thickness of 0.46 ± 0.03 nm2 molecule−1 and 1.75 ± 0.10 nm respectively, the dimensions indicating that the molecules are either less closely packed or more tilted compared with those of the self-assembled film.

  4-2-[N-(10-硫代癸基)喹啉鎓-4-基]乙烯基}苯酚自组装在金上，接触面积为 0.35 ± 0.03 nm2 molecule-1，单层厚度为 1.64 ± 0.07 nm，在 632.8 nm 波长处介电常数分量为 εr ≈ 2.8 和 εi ≈ 0.6。薄膜从紫色（美拉菁形式）变为黄色（质子化形式），通过监测反射率的变化，可用作传感器，对载气中 NH3 的检测限小于 1 ppm。N-octadecyl 类似物的 Langmuir-Blodgett (LB) 薄膜表现出类似的特性，但在传感应用中，由于苯酚基与基底相邻，因此处于劣势。它们的接触面积和单层厚度分别为 0.46 ± 0.03 nm2 molecule-1 和 1.75 ± 0.10 nm。
• Molecular Rectification:  Self-Assembled Monolayers in Which Donor−(π-Bridge)−Acceptor Moieties Are Centrally Located and Symmetrically Coupled to Both Gold Electrodes
  作者：Geoffrey J. Ashwell、Wayne D. Tyrrell、Anne J. Whittam

  DOI：10.1021/ja049633u

  日期：2004.6.1

  Self-assembled monolayers (SAMS) obtained from 1-(10-acetylsulfanyldecyl)-4-[2-(4-dimethylaminophenyl)vinyl]quinolinium iodide exhibit asymmetric current-voltage (I-V) characteristics. The rectification may be reversibly switched: it is suppressed when the film is exposed to HCl vapor, the intramolecular charge-transfer axis being inhibited by protonation, but restored when exposed to NH3. The behavior is intrinsic to the donor- (pi-bridge)-acceptor moiety, and ambiguity in the assignment has been excluded by matching the alkyl tails on the substrate and contacting STM tip to locate the chromophore midway between the electrodes: Au-S-C10H21//D-pi-A-C10H20-S-Au. Films contacted by gold tips exhibit rectification ratios of ca. 18 at +/-1 V, whereas those contacted by pentanethiolate (Au-S-C5H11)- and decanethiolate (Au-S-C10H21)-coated tips have corresponding ratios of ca. 11 and 5, respectively. The I-V curves are different, but when adjusted for thickness the current versus electric field dependence is indistinguishable. Seven dyes are reported: SAMs with sterically hindered D-pi-A moieties, in which the donor and acceptor are twisted out of plane, exhibit rectification, whereas those that are planar or have a weak donor-acceptor combination do not.