Journal
ORGANIC LETTERS
Volume 23, Issue 18, Pages 7003-7007Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00834
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Funding
- Science and Engineering Research Board (SERB), India [ECR/2015/000337, CRG/2019/003299]
- Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR)
- Shiv Nadar University (SNU)
- SNU
- SERB [EMR/2016/000576]
- UGC
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1,2-Dibenzoyl-1-tert-butylhydrazine and related N-alkyl-N,N'-diacylhydrazines are environmentally friendly insect growth regulators. The interactions mediated by a hydrazide amide nitrogen atom play a crucial role in stabilizing their biologically active trans-cis rotameric conformations, as supported by spectroscopic and computational studies.
1,2-Dibenzoyl-1-tert-butylhydrazine (RH-5849) and related N-alkyl-N,N'-diacylhydrazines are environmentally benign insect growth regulators. Herein, we show that an unusual n(N)(amide) -> pi*(Ar) 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.
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