Quantum-chemical studies on geometries of nitrate molecules

Abstract

Semi-empirical SCF-MO calculations by MINDO / 3, MNDO and AM1 have been performed to obtain molecular geometries of 32 nitrates by complete optimization. The results calculated from the three methods are similar to each other. By comparing with the experimental geometries of four compounds (i.e. , methyl nitrate, N-nitrobis (2-hydro- xyethyl)-amine dinitrate, nitroglycerine and pentaerythrite tetranitrate), it is found that AM1 method is better than the other methods for predicting molecular geometry. The -ONO~2 groups in molecules of various nitrates have approximately the same value of geometrical0 parameters. The bond lengths and bond angles of straight-chain alkyl nitrates are akin to each other, and all heavy atoms in the molecules are coplanar at their trans-conformations. The bisubistituted straight-chain and tetrasubstituted ester molecules have symmetrical structures.

Key words: MOLECULAR ORBITAL METHOD, GEOMETRICAL ISOMERISM, NITRATE

CLC Number:

O621.16

Cite this article

Gong Xuedong;YU BAIHENG;WANG DAXI;XIAO HEMING. Quantum-chemical studies on geometries of nitrate molecules[J]. Chin. J. Org. Chem., 1994, 14(3): 274-279.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Bing Mu, Junliang Wu, Guang'an Zhang. Alternative Approach for the Synthesis of Nitroaromatic Olefins via Dehydrogenative Nitration of Easily Available Arylethanes [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 250-257.
[2]	Li Fangyao, Huang Lin, Zhou Xiaoqun, Li Qian, Ma Xianli, Duan Wengui, Wang Xiu. Synthesis and Cytotoxicity Evaluation of Dehydroabietic Acid Derivatives Bearing Nitrate Moiety [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2845-2854.
[3]	Wu Yan, Zhang Yang, Wu Jiajie, Zhou Jun, Liu Hong, Tu Tao. Visual Discrimination of Phosphate Anion via Selective Metallo-Hydrogel Formation [J]. Chin. J. Org. Chem., 2018, 38(3): 705-709.
[4]	Yan Xiaohui, Li Jiarong, Zhang Qi, Shi Daxin. Synthesis of Nitroarenes under Microwave [J]. Chin. J. Org. Chem., 2017, 37(6): 1450-1455.
[5]	BI Fu-Qiang, YAO Jun-Liang, WANG Bo-Zhou, FAN Xue-Zhong, GE Zhong-Xue, XU Cheng, LIU Qing, KANG Bing. Synthesis, Crystal structure and Properties of 2,3-Bis(hydroxymethyl)- 2,3-dinitro-1,4-butanediol Tetranitrate [J]. Chin. J. Org. Chem., 2011, 31(11): 1893-1900.
[6]	ZHANG Yun-Zhi,CHEN Guan-Yu,CHEN Guo-Rong*. An Efficient Synthesis of Brominated C-Aryl Glycopyranoside [J]. Chin. J. Org. Chem., 2008, 28(2): 321-324.
[7]	SONG Jia-Nan^a,LI Xin-Sheng,b,XU Dong-Cheng*^,a,b,CAI Ling-Ling^a. Oxidative Cross-Coupling of Substituted Aryl β-Ketoesters by Cerium Ammonium Nitrate [J]. Chin. J. Org. Chem., 2008, 28(05): 810-813.
[8]	FANG Lei^a,HUANG Zhang-Jian^a,ZHANG Yi-Hua*^,a,JI Hui^b,DING Da-Yong^b. Synthesis, Anti-inflammatory Activity and Safety of Hydrocortisone Derivatives Coupled with Furoxans and Nitrates [J]. Chin. J. Org. Chem., 2008, 28(05): 841-850.
[9]	JIN Wen-Hu, JIN Jing, JI Ya-Fei*. Synthesis of Coenzyme Q₁₀[J]. Chin. J. Org. Chem., 2007, 27(12): 1605-1608.
[10]	WANG Cai-Feng,JIANG Heng*^,1,GONG Hong,WANG Min²,WANG Zhi-Chang². Synthesis of Different 3,4-Dihydropyrimidin-2(1H)-one Cata-lyzed by Inorganic Zinc Compounds [J]. Chin. J. Org. Chem., 2006, 26(03): 333-336.
[11]	Yu Jiugao;Wang Shaomin. Study on the Adsorbing Process of Cellulose Nitrate for Creatinine [J]. Chin. J. Org. Chem., 2003, 23(9): 1033-1035.
[12]	Huang Qimao;Chen Zhangping;Xu Hansheng;Wu Xuanjie;Zhao Yonggang;Zhang Xiaowei. Regioselective synthesis of 2-nitro-5, 10, 15, 20- tetraarylporphyrinato metal [J]. Chin. J. Org. Chem., 2001, 21(10): 746-750.
[13]	Peng Xinhua;Lu Chunxu. Regioselectivity of aromatic nitration (with alkyl nitrates) in the presence of acid-treated bentonite catalysts [J]. Chin. J. Org. Chem., 2000, 20(4): 570-573.
[14]	Wang Daxi;Wang Zhaohui. Quantum chemistry applied to condensation mechanism of formation of alkyl polyethyleneamide [J]. Chin. J. Org. Chem., 2000, 20(4): 587-590.
[15]	LI YEZHI;GUO CHUNXIAO;LANG MEIDONG;ZHAO XIAOGANG;HUANG HUAMIN. Synthesis and crystal structure of (R)-N-acetylthiazolidine- 2-thione-4-carbonyl TT [J]. Chin. J. Org. Chem., 1998, 18(2): 124-129.

硝酸酯分子几何构型的量子化学研究