Topological Study on the Boiling Points of Unsaturated Chain Hydrocarbons

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (2): 173-183. Previous Articles Next Articles

不饱和链烃沸点的拓扑研究

沐来龙^*, 冯长君

徐州师范大学化学系徐州 221006

收稿日期:2003-06-23 修回日期:2003-07-31 接受日期:2003-08-15 发布日期:2022-09-20
基金资助:
江苏省高校自然科学基金(No. 02KJB150008)资助项目

Topological Study on the Boiling Points of Unsaturated Chain Hydrocarbons

MU, Lai-Long^*, FENG, Chang-Jun

Depertment of Chemistry, Xuzhou Normal University, Xuzhou 221009

Received:2003-06-23 Revised:2003-07-31 Accepted:2003-08-15 Published:2022-09-20
Contact: * E-mail: mull@xznu.edu.cn

Abstract

On the basis of adjacent matrix and edge valence (f_i), a novel connectivity index (^mF) was developed. Among ^mF, ⁰F and ¹F showed good structural selectivity for unsaturated chain hydrocarbons. Correlation cofficients between ⁰F, ¹F and the boilingpoints (T_b) of294 unsaturated chain hydrocarbons (with the number of carbon atoms ranging from 2 to 20) were examined and the following regression formula was obtained: ln(700-T_b)=6.52331-0.00488 ⁰F²-0.34677 ¹F^0.5 (n=294,R=0.9979, R²=0.9958, F=34904, S=5.12), which could providesatisfactory estimates and prediction for the boiling points of unsaturatedchain hydrocarbons. Furthermore, the model was examined to validate the modelrobustness with Jackknifed method. All these results showed that the connectivity index (^mF) of edge valenc was a important parameter in QSPR studies.

Key words: connectivity index of edge valence, unsaturated chain hydrocarbon, boiling point, quantitative structure-property relationship

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MU, Lai-Long, FENG, Chang-Jun. Topological Study on the Boiling Points of Unsaturated Chain Hydrocarbons[J]. Chinese Journal of Organic Chemistry, 2004, 24(2): 173-183.

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References

1 Xu, L.; Hu, C. Y. The Applications of Graph Theory inChemistry, Science Press, Beijing, 2000, p. 148 (in Chinese).
(许禄, 胡昌玉, 应用化学图论, 科学出版社, 北京, 2000, p. 148.)
2 Wiener, H. J. Am. Chem. Soc. 1947, 69(1), 17.
3 Hosoya, H. Bull. Chem. Soc. Jpn. 1971, 44, 2332.
4 Randic, M. J. Am. Chem. Soc. 1975, 97,6609.
5 Kier, L. B.; Hall, H. Molecular Connectivity in Chemstry and Drug Research, Academic Press, New York, 1976, p. 18.
6 Balaban, A. T. Pure Appl. Chem. 1983, 55, 199.
7 Estrada, E. J. Chem. Inf. Comput. Sci. 1995, 35(1), 31.
8 Xu, L. Chemometrics Methods, Science Press, Beijing, 1995, p. 355 (in Chinese).
(许禄, 化学计量学方法, 科学出版社, 北京, 1995, p. 355.)
9 Feng, C. J.; Li, M. J.; Chen, Y. Tang, Z. Q. Acta Chim. Sinica 2001, 59(6), 853 (in Chinese).
(冯长君, 李鸣建, 陈艳, 唐自强, 化学学报, 2001, 59(6), 853.)
10 Feng, C. J. Chin. J. Inorg. Chem. 2000, 16(5), 715 (in Chinese).
(冯长君, 无机化学学报, 2000, 16(5), 715.)
11 Feng, C. J.; Chen, Y.; Li, M. J. Chin. J. Org. Chem. 2002, 22(3), 206 (in Chinese).
(冯长君, 陈艳, 李鸣建, 有机化学, 2002, 22(3), 206.)
12 Katritzky, A. R.; Maran, U.; Lobanov, V. S.; Karelson, M. J. Chem. Inf. Comput. Sci. 2000, 40, 1.
13 Katritzky, A. R.; Mu, L.; Lobanov, V. S.; Karelson, M. J. Phys. Chem. 1996, 100, 10400.
14 Katritzky, A. R.; Lobanov, V. S.; Karelson, M. J. Chem. Inf. Comput.Sci. 1998, 38, 28.
15 Mihalic, Z. J. Chem. Inf. Comput. Sci. 1992, 32, 28.
16 Trinajstic, N.; Nikolic, S.; Lucic, B.; Amic. D.; Mihalic, Z. J. Chem. Inf. Comput. Sci. 1997, 37, 631.
17 Bücker, G.; Bücker, C. J. Chem. Inf. Comput. Sci. 1998, 38, 710.
18 Cao, C. Z.; Yuan, H. Chin. J. Org. Chem. 2002, 22(5), 354 (in Chinese).
(曹晨忠, 袁华, 有机化学, 2002, 22(5), 354.)
19 Feng, C. Z.; Chen, J.; Yang, H. X.; Dong, S. Q. Teaching Reference Book (2) of Inorganic Chemistry, Highter Education Press, Beijing, 1985, p. 95 (in Chinese).
(冯慈珍, 陈鉴, 杨宏孝, 董松琦, 无机化学教学参考书(2), 高等教育出版社, 北京, 1985, p. 95.)
20 Robert, C. W.; Jeanette, G. G. Handbook of Data on Organic Compounds, 2nd ed., CRC Press, Boca Raton, Florida, 1989.
21 Feng, C. J.; Du, X. H. Chin. J. Chromatogr. 2001, 19(2), 124 (in Chinese).
(冯长君, 堵锡华, 色谱, 2001, 19(2), 124.)

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[2]	Zhang Yulin;Gao Jinming;Guo Mancai. Study on Quantitative Structure-Property Relationship between Molecular Connectivity Index (~mX~z) and Boiling Points of Aliphatic Unsaturated Hydrocarbons [J]. Chin. J. Org. Chem., 2003, 23(9): 1039-1048.
[3]	Feng Changjun;Wang Chao. Predicting Boiling Points and Thermodynamic Properties for Alkanes with a Topological Index of Square Root of Harmonic Average and Numbers of Path [J]. Chin. J. Org. Chem., 2003, 23(10): 1169-1176.
[4]	Zhang Xiuli;Wang Yongxian;Ji Xinming;Li Junling. Molecular inductive effect index and boiling point of paraffinic hydrocarbons [J]. Chin. J. Org. Chem., 2002, 22(6): 440-445.
[5]	Cao Chenzhong;Yuan Hua. Relationship between molecular structure and boiling point of aliphatic unsaturated hydrocarbons [J]. Chin. J. Org. Chem., 2002, 22(5): 354-363.
[6]	Wang Keqiang;Wang Jie;Feng Ruiying. Group bond contribution-a new method for calculating boiling points of cycloalkanes [J]. Chin. J. Org. Chem., 2002, 22(3): 194-199.
[7]	Zhang Xiuli;Wang Yongxian;Li Junling;Lin Yingwu. Molecular inductive effect index and boiling point of aliphatic aldehydes and alkanones [J]. Chin. J. Org. Chem., 2002, 22(11): 897-901.
[8]	Chen Yan. Study on quantitative structure-property relationship of boiling points of aliphatic aldehydes and alkanones with topological indices of atomic ordinal number [J]. Chin. J. Org. Chem., 2001, 21(3): 242-246.
[9]	Wang Keqiang;Wang Jie. A new group contribution method for calculating the boiling point of alkane [J]. Chin. J. Org. Chem., 2001, 21(10): 751-754.
[10]	Wang Keqiang. Studies on the relationship between boiling points of aldehydes and alkanones and their molecular structures by using molecular topology [J]. Chin. J. Org. Chem., 1998, 18(5): 419-424.
[11]	LI ZHILIANG;CAO CHENZHONG. Effective length of carbon chain and boiling point of fatty alcohols [J]. Chin. J. Org. Chem., 1998, 18(4): 360-364.
[12]	CAO CHENZHONG;KONG CHUNHUI. Effective length of carbon chain and boiling point of paraffinic hydrocarbons [J]. Chin. J. Org. Chem., 1997, 17(4): 324-328.
[13]	WANG KEQIANG;HU YING. Studies on the relationship between boiling point of mercaptan and thioether and their molecular structure [J]. Chin. J. Org. Chem., 1997, 17(3): 230-233.

不饱和链烃沸点的拓扑研究

Topological Study on the Boiling Points of Unsaturated Chain Hydrocarbons

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