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Published on: October 24, 2017
3-tert-Butyl-5,6,8-trinitro-naphtho[1,8a,8-cd][1,2]dithiole
Yuqin Jiang1, Xiangjian Wan, Yongsheng Chen
1Key Laboratory for Functional Polymer Materials and Center for Nanoscale Science and Technology, Institute of Polymer Chemistry, College of Chemistry, Nankai University, Weijin Road No. 94, Tianjin, People's Republic of China.
Nitration of a naphthalene disulfide yielded a new compound, C(14)H(11)N(3)O(6)S(2). This molecule forms a tape-like structure through weak interactions between sulfur and nitro group oxygen atoms.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Naphthalene derivatives are versatile organic compounds.
- Disulfide compounds can exhibit unique structural properties.
- Nitration is a common method for functionalizing aromatic rings.
Purpose of the Study:
- To synthesize and characterize a novel nitrated naphthalene disulfide.
- To investigate the intermolecular interactions and crystal packing of the synthesized compound.
Main Methods:
- Chemical synthesis involving the nitration of 2,7-di-tert-butyl-naphthalene 1,8-disulfide using fuming nitric acid.
- Single-crystal X-ray diffraction to determine the molecular structure and crystal packing.
Main Results:
- Successful synthesis of the title compound, C(14)H(11)N(3)O(6)S(2).
- Identification of a tape motif formed by weak head-to-tail intermolecular interactions (3.131 Å) between sulfur and nitro group oxygen atoms.
- Detailed structural analysis revealing the specific arrangement of molecules in the crystal lattice.
Conclusions:
- The nitration reaction provides a route to novel functionalized naphthalene disulfides.
- The observed tape motif highlights the role of weak interactions in directing supramolecular assembly.
- The study contributes to understanding the structure-property relationships in sulfur-containing aromatic compounds.
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