Evidence of an n N (amide) → π Ar Interaction in N -Alkyl- N , N '-diacylhydrazines

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...

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Bibliographic Details
Published in:Organic letters 2021-09, Vol.23 (18), p.7003-7007
Main Authors: Deka, Jugal Kishore Rai, Sahariah, Biswajit, Sakpal, Sushil S, Bar, Arun Kumar, Bagchi, Sayan, Sarma, Bani Kanta
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00834