DFT STUDIES OF STRUCTURAL PARAMETERS, VIBRATIONAL FREQUENCIES AND NMR SPECTRA OF 3-(1H-BENZO[D]IMIDAZOL-1-YL)-N'-(TOSYLOXY)PROPANIMIDAMIDE

E. Yergaliyeva, L. Kayukova, A. Vologzhanina, G. Baitursynova, V. Vazhev
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Abstract

Amidoxime derivatives have practically valuable biological properties. We have previously obtained new spiropyrazolinium compounds by arylsulfo-chlorination of β-aminopropioamidoximes, but in case of β-(benzimidazol-1-yl)pro-pioamidoxime we have obtained O-substitution product – 3-(1H-benzo[d]imidazol-1-yl)-N'-(tosyloxy)pro-panimidamide. The aim of the work is predicting of structural parameters (bond lengths, bond angles), vibrational frequencies and NMR spectra of 3-(1H-benzo-[d]imidazol-1-yl)-N'-(tosyloxy)propanimidamide. The calculations were performed using Gaussian 09 package. Structural parameters and vibrational frequencies was calculated using DFT (B3LYP/B3PW91/WB97XD)/6-31G(d,p). 1H and 13C NMR was predicted using DFT B3LYP/6-31G(d,p)-GIAO in DMSO. All calculated values are in good agreement with experimental data. The calculated bond lengths and bond angles were compared with results of X-ray structural analysis. The best correlation coefficient was 0.981 (calcu-lations with B3LYP level). For bond angles, the best result was obtained with B3LYP level (0.990). For vibrational frequencies correlation coefficients between the calculated and experimental values were 0.997 (B3LYP), 0.996 (B3PW91) and 0.995 (WB97XD). The most accurate method was used for predic-ting NMR spectrum. The correlation coefficients between the experimental and calculated 1H and 13C chemical shifts were 0.949 and 0.999 respectively.
3-(1h -苯并[d]咪唑-1-基)- n′-(tosyloxy)咪唑酰胺结构参数、振动频率和核磁共振谱的DFT研究
偕胺肟衍生物具有重要的生物学特性。我们以前用芳基磺化氯化法得到了新的螺吡唑啉化合物,但对于β-(苯并咪唑-1-基)原吡唑胺,我们得到了o取代产物- 3-(1h -苯并咪唑-1-基)- n '-(tosyloxy)原吡唑胺。这项工作的目的是预测3-(1h -苯并-[d]咪唑-1-基)- n '-(tosyloxy)丙酰胺的结构参数(键长,键角),振动频率和核磁共振波谱。使用Gaussian 09软件包进行计算。采用DFT (B3LYP/B3PW91/WB97XD)/6-31G(d,p)计算结构参数和振动频率。用DFT B3LYP/6-31G(d,p)-GIAO在DMSO中预测1H和13C核磁共振。计算值与实验数据吻合较好。将计算得到的键长和键角与x射线结构分析结果进行比较。最佳相关系数为0.981(以B3LYP水平计算)。对于键角,以B3LYP水平(0.990)为最佳。振动频率计算值与实验值的相关系数分别为0.997 (B3LYP)、0.996 (B3PW91)和0.995 (WB97XD)。采用最准确的方法预测核磁共振谱。1H和13C化学位移与实验计算值的相关系数分别为0.949和0.999。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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