Structure-Reactivity-Spectra Correlations for Substituted Benzenesulfonamides

A. Perjéssy, E. Kolehmainen, W. Fabian, M. Ludwig, K. Laihia, J. Kulhanek, Z. Šusteková
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引用次数: 4

Abstract

The infrared absorption bands of the S=O and N-H stretching vibrations as well as the natural abundance 13 C and the 17 O NMR chemical shifts were measured for fifteen substituted benzenesulfonamides in CDCl 3 and acetone-d 6 . For the unsubstituted compound the natural abundance 33 S NMR chemical shift was also measured in acetone-d 6 PM3 charge densities and bond orders were calculated for the completely optimised geometry. Mutual correlations are reported between the wave numbers of the asymmetric SO 2 stretching vibration, the arithmetic means of symmetric and asymmetric NH 2 stretching vibrations, Hammett or + substituent constants, dissociation constants, 1 H, 13 C, 15 N and 17 O NMR chemical shifts as well as the PM3 S=O and N-H bond orders and hydrogen, nitrogen and oxygen atom charge densities. The results of the correlation analysis showed that the factors determining the electronic structure and controlling the dissociation equilibria, the IR and NMR spectral properties of substituted benzenesulfonamides must be the same.
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取代苯磺酰胺的结构-反应-光谱相关性
测定了15种取代苯磺酰胺在cdcl3和丙酮- d6中的S=O和N-H伸缩振动的红外吸收带以及13c的自然丰度和17o的核磁共振化学位移。对于未被取代的化合物,在丙酮-d中也测量了天然丰度33 S NMR化学位移6 PM3的电荷密度和键序,计算了完全优化的几何形状。本文报道了不对称so2拉伸振动的波数、对称和不对称nh2拉伸振动的算术平均值、Hammett or +取代基常数、解离常数、1 H、13 C、15 N和17 O核磁共振化学位移以及PM3 S=O和N-H键序与氢原子、氮原子和氧原子电荷密度之间的相互关系。相关分析结果表明,取代苯磺酰胺的电子结构的决定因素和解离平衡的控制因素、红外光谱和核磁共振光谱性质都是相同的。
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