Molecular structure of di-aryl-aldimines by multinuclear magnetic resonance and X-ray diffraction

作者: Rubén Montalvo-González , Armando Ariza-Castolo

DOI: 10.1016/S0022-2860(03)00279-5

关键词:

摘要: The complete 1H, 13C and 15N NMR analyses for a series of 25 diaryl-aldimines containing phenyl, pyridyl, pyrazolone furanyl moieties are described herein. Detailed evaluation substituent chemical shift coupling constant effects showed that interaction between the lone pair carbonyl group or nitrogen 2-substitued pyridines with aldimine hydrogen increases 1JCH value shifts resonance signal this to high frequency, in 1H spectra. X-ray crystal structure analysis substituted aldimines evidenced planarity aryl groups which conjugated CyN double bond. In case N-(2-pyridinemethylene)-1,5 dimethyl-2-phenyl-1,2- dihydro-pyrazol-3-one, two rotamers were observed same unit cell.

参考文章(52)
NOBUYA KATAGIRI, YUTAKA MIURA, RYUJI NIWA, TETSUZO KATO, Studies on Ketene and Its Derivatives. CXII. Reaction of Ketene with Schiff Bases to give α-Unsubstituted β-Lactams Chemical & Pharmaceutical Bulletin. ,vol. 31, pp. 538- 544 ,(1983) , 10.1248/CPB.31.538
Derek R. Boyd, Michael E. Stubbs, N. J. Thompson, Herman J. C. Yeh, Donald M. Jerina, Roderick E. Wasylishen, Nitrogen‐15 coupling constants: Geminal coupling, 2J(15NH), in cis‐ and trans‐aldonitrones and vicinal coupling, 3J(15NH), in cis‐and trans‐ketimines, oxaziridines and nitrones Magnetic Resonance in Chemistry. ,vol. 14, pp. 528- 533 ,(1980) , 10.1002/MRC.1270140620
Gerald W. Buchanan, Brian A. Dawson, Aromatic imine stereochemistry as studied by13C and1H NMR of15N-enriched materials Organic Magnetic Resonance. ,vol. 13, pp. 293- 298 ,(1980) , 10.1002/MRC.1270130416
Thomas Freier, Manfred Michalik, Klaus Peseke, Helmut Reinke, NMR studies on intramolecular mobility of ortho-substituted push-pull phenyl butadienes† Journal of The Chemical Society-perkin Transactions 1. pp. 1265- 1272 ,(1999) , 10.1039/A805857A
Hans-Peter Erb, Thorsten Bluhm, 13C NMR spectra of diazastilbenes. I—trans-styryldiazines Magnetic Resonance in Chemistry. ,vol. 14, pp. 285- 289 ,(1980) , 10.1002/MRC.1270140413
Stefan Schunk, Dieter Enders, Solid-phase synthesis of beta-lactams via the ester enolate-imine condensation route. Organic Letters. ,vol. 2, pp. 907- 910 ,(2000) , 10.1021/OL0055465
Zhong-Heng Yu, Xiao-Qi Peng, New Insight into the Nature of Electron Delocalization: the Driving Forces for Distorting the Geometry of Stilbene-Like Species Journal of Physical Chemistry A. ,vol. 105, pp. 8541- 8553 ,(2001) , 10.1021/JP011487G