Browse > Article
http://dx.doi.org/10.5012/bkcs.2009.30.10.2351

Use of Correlation of 1H and 13C Chemical Shifts of N-Arylsuccinanilic Acids,N-Arylsuccinimides, N-Arylmaleanilic Acids, and N-Arylmaleimides with the Hammett Substituent Constants for the Studies of Electronic Effects  

Lee, Hye-Sun (Department of Chemistry, Kangwon National University)
Yu, Ji-Sook (Department of Chemistry, Kangwon National University)
Lee, Chang-Kiu (Department of Chemistry, Kangwon National University)
Publication Information
Abstract
A series of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides was prepared and their NMR spectra were examined by correlating the $^1H\;and\;^{13}C$ chemical shift values with the corresponding Hammett $\sigma$ values. The carbonyl carbons of the amides show a normal correlation with $\sigma$ but those of the imides show an inverse correlation.
Keywords
Correlation of chemical shifts; Succinanilic acid; Succinimide; Maleanilic acid; Maleimide;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By Web Of Science : 1  (Related Records In Web of Science)
Times Cited By SCOPUS : 1
연도 인용수 순위
1 Jeon, K. O.; Yu, J. S.; Lee, C. K. J. Heterocyclic Chem, 2003, 40, 763-771.   DOI   ScienceOn
2 Jeon, K. O.; Yu, J. S.; Lee, C. K. Bull. Korean Chem. Soc. 2002, 23, 1241-1246.   DOI   ScienceOn
3 Lee, C. K.; Yu, J.S.; Lee, H.-J. J. Heterocyclic Chem. 2002, 39, 1207-1217.   DOI   ScienceOn
4 Lee, C. K.; Yu, J. S.; Ji, Y. R. J. Heterocyclic Chem. 2002, 39, 1219-1227.   DOI   ScienceOn
5 Akalay, D.; Duerner, G.; Goebel, M. W. Eur. J. Org. Chem. 2008, 2365-2368.
6 Hoshino, M.; Matsuzaki, H.; Fujita, R. Chem. Pharm. Bull. 2008, 56, 480-484.   DOI   ScienceOn
7 Yu, H.; Lee, P. H. J. Org. Chem. 2008, 73, 5183-5186   DOI   ScienceOn
8 Chou, S.-S. P.; Wang, H.-C.; Chen, P.-W.; Yang, C.-H. Tetrahedron 2008, 64, 5291-5297.   DOI   ScienceOn
9 Bojase, G.; Payne, A. D.; Willis, A. C.; Sherburn, M. S. Angew. Chem. Int. Ed. 2008, 47, 910-912.   DOI   ScienceOn
10 Kluger, R.; Hunt, J. C. J. Am. Chem. Soc. 1989, 111, 5921-5925.   DOI
11 Martin, S. F.; Limberakis, C. Tetrahedron Lett. 1997, 38, 2617-2620.   DOI   ScienceOn
12 Le, Z.-G.; Chen, Z.-C.; Hu, Y.; Zheng, Q.-G. Synthesis 2004, 995-998.
13 Lan, J.-B.; Zhang, G.-L.; Yu, X.-Q.; You, J.-S.; Chen, L.; Yan, M.; Xie, R.-G. Synlett 2004, 1095-1097.
14 Pal, B.; Pradhan, P. K.; Jaisankar, P.; Giri, V. S. Synthesis 2003, 1549-1552.
15 Al-Mousawi, S. M.; EL-Apasery, M. A.; Elnagdi, M. H. Heterocycles 2008, 75, 1151-1161.   DOI   ScienceOn
16 Metwally, N. H. Heterocycles 2008, 75, 319-329.   DOI   ScienceOn
17 Kar, A.; Argade, N. P. Synthesis 2002, 221-224.
18 Cava, M. P.; Deana, A. A.; Muth, K.; Mitchell, M. J. Org. Syn. Col. Vol. V 1973, 944-946.
19 Kishikawa, K.; Naruse, M.; Kohmoto, S.; Yamamoto, M.; Yamaguchi, K. J. Chem. Soc. Perkin Trans. 1 2001, 462-468.
20 Keana, J. F. W.; Ogan, M. D.; Lu, Y.; Beer, M.; Varkey, J. J. Am. Chem. Soc. 1986, 108, 7957-7963.   DOI
21 Craik, D. J.; Brwonlee, R. T. C. Prog. Phys. Org. Chem. 1983, 14, Chapter 1.
22 $\sigma$ values are taken from reference 6, p 321
23 Yuzuri, T.; Suezawa, H.; Hirota, M. Bull. Chem. Soc. Jpn. 1994, 67, 1664-1673.   DOI   ScienceOn
24 Jeon, K. O.; Yu, J. S.; Lee, C. K. Heterocycles 2007, 71, 153-164.   DOI   ScienceOn
25 Cis-coupling constant ranges 6 to 15 Hz: Pavia, D. L.; Lampman, G. M.; Kriz, G. S.; Vyvyan, J. R. Introduction to Spectroscopy, $4^{th}^$ Ed.; Brooks/Cole: Belmont, CA, 2009; p 140.
26 Lee, H. S.; Yu, J. S.; Lee, C. K. Magn. Reson. Chem. 2009, 47, 711-715.   DOI   ScienceOn
27 Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; John Wiley & Sons: New York, 1984; pp 311-325.
28 Mederski, W. W. K. R.; Baumgarth, M.; Germann, M.; Kux, D.; Weitzel, T. Tetrahedron Lett. 2003, 44, 2133-2136.   DOI   ScienceOn
29 Brummond, K. M.; Chen, D.; Painter, T. O.; Mao, S.; Seifried, D. D. Synlett 2008, 759-764.
30 Lee, C. K.; Lee, I.-S. H. Bull. Korean Chem. Soc. 2008, 29, 2205-2208.   DOI   ScienceOn