Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Dadri, Uttar Pradesh 201314, India.
New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Jakkur, Bangalore 560064, India.
Org Lett. 2021 Sep 17;23(18):7003-7007. doi: 10.1021/acs.orglett.1c00834. Epub 2021 May 11.
1,2-Dibenzoyl-1--butylhydrazine (RH-5849) and related -alkyl-,'-diacylhydrazines are environmentally benign insect growth regulators. Herein, we show that an unusual n(amide) → π* interaction mediated by a hydrazide amide nitrogen atom plays a crucial role in stabilizing their biologically active trans-cis (t-c) rotameric conformations. We provide NMR and IR spectroscopic evidence for the presence of these interactions, which is also supported by X-ray crystallographic and computational studies.
1,2-二苯甲酰基-1--丁基酰肼（RH-5849）和相关的 -烷基-,'-二酰基酰肼是环境友好型昆虫生长调节剂。在这里，我们表明，一种不寻常的 n(酰胺) → π* 相互作用通过酰肼酰胺氮原子介导，在稳定它们具有生物活性的反式-顺式（t-c）构象旋转异构体中起着至关重要的作用。我们提供了这些相互作用存在的 NMR 和 IR 光谱证据，这也得到了 X 射线晶体学和计算研究的支持。
