Evidence of an nN(amide) → π*Ar Interaction in N-Alkyl-N,N′-diacylhydrazines

Please use this identifier to cite or link to this item: https://hdl.handle.net/20.500.12252/6249

Title:	Evidence of an nN(amide) → π*Ar Interaction in N-Alkyl-N,N′-diacylhydrazines
Authors:	Bagchi, Sayan Rai Deka, Jugal Kishore Sahariah, Biswajit Sakpal, Sushil Bar, Arun Kumar Bagchi, Sayan Sarma, Bani Kanta
Issue Date:	11-May-2021
Publisher:	Organic Letters
Abstract:	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 nN(amide) → π*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.
URI:	https://hdl.handle.net/20.500.12252/6249
Appears in Collections:	NCL Publications

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