1-(Anthracen-9-ylmethylideneamino)-3-cyclohexylthiourea | 473273-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(Anthracen-9-ylmethylideneamino)-3-cyclohexylthiourea
• CAS: 473273-82-4
• 化学式: C₂₂H₂₃N₃S
• 分子量: 361.511
• InChiKey: DANRPPRKZZPGPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(Anthracen-9-ylmethylideneamino)-3-cyclohexylthiourea 在 氢氟酸 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Spectroscopic and TD-DFT studies on the turn-off fluorescent chemosensor based on anthraldehyde N(4) cyclohexyl thiosemicarbazone for the selective recognition of fluoride and copper ions

  摘要：

  The copper and fluoride ions sensing mechanism of a chemosensor based on anthraldehyde N(4) cyclohexyl thiosemicarbazone (AntCy) was investigated via colorimetric, fluorescence, electrochemical and NMR titration studies. Detailed investigations on their sensing mechanism was done using DFT and TD-DFT studies. H-1 NMR titration shows deprotonation of NH protons by fluoride ion is a prominent step in naked eye recognition. The Gibbs free energy of overall sensing reaction has moderate transition barrier with 18.19 kcal mol(-1). Using the vibrational frequency analysis, all the local minima of ground state and excited state were confirmed. Due to the small size and strong electronegativity of fluoride, an intramolecular hydrogen bonding interaction with N(3)-H, which is closer to anthracene moiety was found to be preferentially formed. The excited state proton transfer mechanism was further confirmed with donor-acceptor interactions using Natural Bond Orbital (NBO) analysis and Potential Energy Surface (PES) analysis. The ICT mechanism for copper ion sensing was also confirmed with TD-DFT calculations. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2016.01.021
• 作为产物：
  描述：

  环己基异硫氰酸脂 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.0h， 生成 1-(Anthracen-9-ylmethylideneamino)-3-cyclohexylthiourea
  参考文献：
  名称：

  Spectroscopic and TD-DFT studies on the turn-off fluorescent chemosensor based on anthraldehyde N(4) cyclohexyl thiosemicarbazone for the selective recognition of fluoride and copper ions

  摘要：

  The copper and fluoride ions sensing mechanism of a chemosensor based on anthraldehyde N(4) cyclohexyl thiosemicarbazone (AntCy) was investigated via colorimetric, fluorescence, electrochemical and NMR titration studies. Detailed investigations on their sensing mechanism was done using DFT and TD-DFT studies. H-1 NMR titration shows deprotonation of NH protons by fluoride ion is a prominent step in naked eye recognition. The Gibbs free energy of overall sensing reaction has moderate transition barrier with 18.19 kcal mol(-1). Using the vibrational frequency analysis, all the local minima of ground state and excited state were confirmed. Due to the small size and strong electronegativity of fluoride, an intramolecular hydrogen bonding interaction with N(3)-H, which is closer to anthracene moiety was found to be preferentially formed. The excited state proton transfer mechanism was further confirmed with donor-acceptor interactions using Natural Bond Orbital (NBO) analysis and Potential Energy Surface (PES) analysis. The ICT mechanism for copper ion sensing was also confirmed with TD-DFT calculations. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2016.01.021

文献信息

• Effect of substitution at N″-position of N′-hydroxy-N-amino guanidines on tumor cell growth
  作者：Arijit Basu、Barij Nayan Sinha、Philipp Saiko、Thomas Szekeres

  DOI：10.1016/j.bmcl.2012.06.048

  日期：2012.8

  Structural modification of one of our earlier reported lead molecule (ABNM13) has been carried out to study the effect of different substituents at the N ''-position of N-hydroxy-N'-amino guanidines (HAGs) on their anticancer activity. Compounds with electron donating substituents were found to be less active. In contrast, those with electron withdrawing groups were found favorable for anticancer activity. The obtained results provide significant SAR information that may be useful for further drug designing with HAGs. (c) 2012 Elsevier Ltd. All rights reserved.
• Spectroscopic and TD-DFT studies on the turn-off fluorescent chemosensor based on anthraldehyde N(4) cyclohexyl thiosemicarbazone for the selective recognition of fluoride and copper ions
  作者：Sabeel M. Basheer、Anthony C. Willis、Ron J. Pace、Anandaram Sreekanth

  DOI：10.1016/j.poly.2016.01.021

  日期：2016.4

  The copper and fluoride ions sensing mechanism of a chemosensor based on anthraldehyde N(4) cyclohexyl thiosemicarbazone (AntCy) was investigated via colorimetric, fluorescence, electrochemical and NMR titration studies. Detailed investigations on their sensing mechanism was done using DFT and TD-DFT studies. H-1 NMR titration shows deprotonation of NH protons by fluoride ion is a prominent step in naked eye recognition. The Gibbs free energy of overall sensing reaction has moderate transition barrier with 18.19 kcal mol(-1). Using the vibrational frequency analysis, all the local minima of ground state and excited state were confirmed. Due to the small size and strong electronegativity of fluoride, an intramolecular hydrogen bonding interaction with N(3)-H, which is closer to anthracene moiety was found to be preferentially formed. The excited state proton transfer mechanism was further confirmed with donor-acceptor interactions using Natural Bond Orbital (NBO) analysis and Potential Energy Surface (PES) analysis. The ICT mechanism for copper ion sensing was also confirmed with TD-DFT calculations. (C) 2016 Elsevier Ltd. All rights reserved.