Synthesis, Single Crystal Structure and 1H NMR Characterization of 3-(2-p-Methylphenylvinyl)-5(4H)-isoxazolone and Theoretical Study for Its Isomerization

Abstract

Abstract: p-Methylphenylvinyl)-5(4H)-isoxazolone was synthesized by the reaction of methylthio ester with NH₂OH·HCl at room temperature and its structure was characterized by single crystal X-ray diffraction. The configuration based on 1H NMR spectrum in CDCl₃ is in agreement with the crystal structure, which indicates that the titled compound is stable in poorly polar solvents, such as diethyl ether and CHCl 3. For 3-(p-methylphenylvinyl)-5(4H)-isoxazolone, the net-charge of C7 is -0.077 and that of C8 is -0.101 by semi-experiential calculations with AM1 and PM3 methods, which are responsible for the chemical shift of H7(6.83) and H8(6.96). With the B3LYP/6-311G^** calculation, the 3-(p-Methylphenylvinyl)-5(4H)-isoxazolone is the most stable configuration among the three isomers.

Key words: 5(4H)-Isoxazolone, Synthesis, Single crystal structure, Theoretical calculation

CLC Number:

O621

TrendMD:

HUANG Kun-Lin, LI Cai-Jin, LIU Qun, BAI Hong-Tao, MU Zhong-Cheng . Synthesis, Single Crystal Structure and ¹H NMR Characterization of 3-(2-p-Methylphenylvinyl)-5(4H)-isoxazolone and Theoretical Study for Its Isomerization[J]. Chem. J. Chinese Universities, 2004, 25(7): 1264.

[1]	CAO Shujie, LI Hongjun, GUAN Wenli, REN Mengtian, ZHOU Chuanzheng. Progress on the Stereocontrolled Synthesis of Phosphorothioate Oligonucleotides [J]. Chem. J. Chinese Universities, 2022, 43(Album-4): 20220304.
[2]	YAO Qing, YU Zhiyong, HUANG Xiaoqing. Progress in Synthesis and Energy-related Electrocatalysis of Single-atom Catalysts [J]. Chem. J. Chinese Universities, 2022, 43(9): 20220323.
[3]	WANG Ruyue, WEI Hehe, HUANG Kai, WU Hui. Freezing Synthesis for Single Atom Materials [J]. Chem. J. Chinese Universities, 2022, 43(9): 20220428.
[4]	WEI Chunhong, JIANG Qian, WANG Panpan, JIANG Chengfa, LIU Yuefeng. Atomic Scale Investigation of Pt Atoms/clusters Promoted Co-catalyzed Fischer-Tropsch Synthesis [J]. Chem. J. Chinese Universities, 2022, 43(8): 20220074.
[5]	JIN Ruiming, MU Xiaoqing, XU Yan. Bio-chemical Synthesis of Melanin Precursor—— 5，6-Dihydroxyindole（DHI） [J]. Chem. J. Chinese Universities, 2022, 43(8): 20220134.
[6]	ZHANG Xinxin, XU Di, WANG Yanqiu, HONG Xinlin, LIU Guoliang, YANG Hengquan. Effect of Mn Promoter on CuFe-based Catalysts for CO₂ Hydrogenation to Higher Alcohols [J]. Chem. J. Chinese Universities, 2022, 43(7): 20220187.
[7]	ZHOU Zixuan, YANG Haiyan, SUN Yuhan, GAO Peng. Recent Progress in Heterogeneous Catalysts for the Hydrogenation of Carbon Dioxide to Methanol [J]. Chem. J. Chinese Universities, 2022, 43(7): 20220235.
[8]	LI Yidi, TIAN Xiaochun, LI Junpeng, CHEN Lixiang, ZHAO Feng. Electron Transfer on the Semiconductor-microbe Interface and Its Environmental Application [J]. Chem. J. Chinese Universities, 2022, 43(6): 20220089.
[9]	LIU Qingqing, WANG Pu, WANG Yongshuai, ZHAO Man, DONG Huanli. Synthesis and Topochemical Polymerization Study of Naphthalene/perylene Imides Substituted Diacetylene Derivatives [J]. Chem. J. Chinese Universities, 2022, 43(6): 20220091.
[10]	LU Cong, LI Zhenhua, LIU Jinlu, HUA Jia, LI Guanghua, SHI Zhan, FENG Shouhua. Synthesis， Structure and Fluorescence Detection Properties of a New Lanthanide Metal-Organic Framework Material [J]. Chem. J. Chinese Universities, 2022, 43(6): 20220037.
[11]	ZHUANG Jiahao, WANG Dingsheng. Current Advances and Future Challenges of Single-atom Catalysis [J]. Chem. J. Chinese Universities, 2022, 43(5): 20220043.
[12]	FENG Li, SHAO Lanxing, LI Sijun, QUAN Wenxuan, ZHUANG Jinliang. Synthesis of Ultrathin Sm-MOF Nanosheets and Their Visible-light Induced Photodegradation of Mustard Simulant [J]. Chem. J. Chinese Universities, 2022, 43(4): 20210867.
[13]	ZHOU Ying, HE Peinan, FENG Haisong, ZHANG Xin. Optimal Distribution of Active Sites of CO₂ Reduction Reaction Catalyzed by Diatomic Site M-N-C [J]. Chem. J. Chinese Universities, 2022, 43(2): 20210640.
[14]	ZHANG Zhinan, CHENG Haiming, TENG Shiyong, ZHANG Ying. Synthesis and Optical Properties of RbPb₂Cl₅ [J]. Chem. J. Chinese Universities, 2022, 43(11): 20220418.
[15]	XING Peiqi, LU Tong, LI Guanghua, WANG Liyan. Controllable Syntheses of Two Cd（II） Metal-organic Frameworks Possessing Related Structures [J]. Chem. J. Chinese Universities, 2022, 43(10): 20220218.

Synthesis, Single Crystal Structure and ¹H NMR Characterization of 3-(2-p-Methylphenylvinyl)-5(4H)-isoxazolone and Theoretical Study for Its Isomerization

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments