AM1 Study on the Mechanism of Catalytic Hydrogenation of 3-Anilinomethy lidene-6-alkyl-5,6-2H-dihydropyran-2,4-diones

Chem. J. Chinese Universities ›› 2001, Vol. 22 ›› Issue (9): 1506.

• Articles • Previous Articles Next Articles

AM1 Study on the Mechanism of Catalytic Hydrogenation of 3-Anilinomethy lidene-6-alkyl-5,6-2H-dihydropyran-2,4-diones

FANG Ya-Yin^1,2, SHEN Rong-Xin², SUN Hong-Wei², YUAN Man-Xue², LIU Jie-LI Zheng-Ming^2,3, LAI Cheng-Ming^2,3

1. Department of Chemistry, Xuzhou Normal University, Xuzhou 221009, China;
2. College of Chemistry, Nankai University, Tianjin 300071, China;
3. State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianj in 300071, China

Received:2000-08-19 Online:2001-09-24 Published:2001-09-24

Abstract

Abstract: 3-(p-Methyl) anilinomethylidene 6-methyl 5,6-Hdihydropyran-2,4-dione was selected as model reactant to study the mechanism of catalytic hydrogenation of 3-anilinomethylidene 6-alkyl-5,6-2Hdihydropyran-2,4-diones by means of the AM1 and UHF/6-311Gmethods. The molecular informations such as heats of formation, net charges, bond orders, the values of frontier orbital energies, composition, their proportion and bonding contribution were acquired and analyzed. Thus the possible reactive sites were put forward and the reaction mechanism was postulated via two steps. The postulated intermediates and products of the two steps were also computed by AM1 method. Their heats of formation and energies of HOMO/LOMO/LUMOindicate that the mechanism of catalytic hydrogenation of 3-anilinomethylidene 6-alkyl-5,6-2Hdihydropyran-2,4-diones is not only a hydrogenolytic addition on CCbond but also a hydrogenolytic cleavage of the C-Nbond of anilinomethylidene.

Key words: AM1, Catalytic hydrogenation, Reaction mechanism, Dihydropyran-2,4-dione

CLC Number:

O626

TrendMD:

FANG Ya-Yin, SHEN Rong-Xin, SUN Hong-Wei, YUAN Man-Xue, LIU Jie-LI Zheng-Ming, LAI Cheng-Ming . AM1 Study on the Mechanism of Catalytic Hydrogenation of 3-Anilinomethy lidene-6-alkyl-5,6-2H-dihydropyran-2,4-diones[J]. Chem. J. Chinese Universities, 2001, 22(9): 1506.

[1]	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.
[2]	YANG Dan, LIU Xu, DAI Yihu, ZHU Yan, YANG Yanhui. Research Progress in Electrocatalytic CO₂ Reduction Reaction over Gold Clusters [J]. Chem. J. Chinese Universities, 2022, 43(7): 20220198.
[3]	SUN Cuihong, LYU Liqiang, LIU Ying, WANG Yan, YANG Jing, ZHANG Shaowen. Mechanism and Kinetics on the Reaction of Isopropyl Nitrate with Cl， OH and NO₃ Radicals [J]. Chem. J. Chinese Universities, 2022, 43(2): 20210591.
[4]	CHENG Yuanyuan, XI Biying. Theoretical Study on the Fragmentation Mechanism of CH₃SSCH₃ Radical Cation Initiated by OH Radical [J]. Chem. J. Chinese Universities, 2022, 43(10): 20220271.
[5]	MENG Fanwei, GAO Qi, YE Qing, LI Chenxi. Potassium Poisoning Mechanism of Cu-SAPO-18 Catalyst for Selective Catalytic Reduction of NO_x by Ammonia [J]. Chem. J. Chinese Universities, 2021, 42(9): 2832.
[6]	YANG Yiying, ZHU Rongxiu, ZHANG Dongju, LIU Chengbu. Theoretical Study on Gold-catalyzed Cyclization of Alkynyl Benzodioxin to 8-Hydroxy-isocoumarin [J]. Chem. J. Chinese Universities, 2021, 42(7): 2299.
[7]	LI Xinyi, LIU Yongjun. Theoretical Insights into the Cleavage of β-Hydroxy Ketone Catalyzed by Artificial Retro-aldolase RA95.5-8F [J]. Chem. J. Chinese Universities, 2021, 42(7): 2306.
[8]	FAN Ye, HAN Huihui, FANG Yun, FENG Ruiqin, XIA Yongmei. Facile Synthesis of Hollow Nickel Submicrospheres with Hierarchical Nano-structure and Its Catalytic Hydrogenation of Phenol [J]. Chem. J. Chinese Universities, 2021, 42(6): 1801.
[9]	REN Ying, LI Changhua, WANG Tao, XUE Shanshan, ZHANG Tingting, JIA Jianfeng, WU Haishun. Theoretical Studies on Pd-catalyzed Oxidative N─H Carbonylation to Synthesis of 1，3，4-Oxadiazole-2（3H）-one Heterocyclic Compounds [J]. Chem. J. Chinese Universities, 2021, 42(6): 1793.
[10]	LI Yiwei, SHENTU Jiangtao, WANG Jingbo, LI Xiangyuan. Combustion Mechanism Construction Based on Minimized Reaction Network： C1⁃Oxygen Combustion [J]. Chem. J. Chinese Universities, 2021, 42(6): 1871.
[11]	TIAN Shengqiao, WEI Meiju. Reaction Mechanism for Rh（Ⅱ）-catalyzed ［3+3］ Cyclization of Indole Derivatives and Propertis of Product [J]. Chem. J. Chinese Universities, 2021, 42(6): 1899.
[12]	QI Guodong, YE Xiaodong, XU Jun, DENG Feng. Progress in NMR Studies of Carbohydrates Conversion on Zeolites [J]. Chem. J. Chinese Universities, 2021, 42(1): 148.
[13]	LI Xiangyuan, SHENTU Jiangtao, LI Yiwei, LI Juanqin, WANG Jingbo. Combustion Mechanism Construction Based on Minimized Reaction Network: Hydrogen-Oxygen Combustion ^† [J]. Chem. J. Chinese Universities, 2020, 41(4): 772.
[14]	LI Xiangyuan,YAO Xiaoxia,SHENTU Jiangtao,SUN Xiaohui,LI Juanqin,LIU Mingxia,XU Shimin. Combustion Reaction Mechanism Construction by Two-parameter Rate Constant Method ^† [J]. Chem. J. Chinese Universities, 2020, 41(3): 512.
[15]	ZHANG Lin, ZHANG Wei, YUE Xin, LI Pengjie, YANG Zuoyin, PU Min, LEI Ming. Theoretical Study on Mechanism of CO₂ Hydrogenation to Formic Acid Catalyzed by Manganese Complex ^† [J]. Chem. J. Chinese Universities, 2019, 40(9): 1911.

AM1 Study on the Mechanism of Catalytic Hydrogenation of 3-Anilinomethy lidene-6-alkyl-5,6-2H-dihydropyran-2,4-diones

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments