%0 Journal Article %J Organic letters %D 2021 %T Evidence of an nN(amide) → π*Ar interaction in N-Alkyl-N,N′-diacylhydrazines %A Deka, Jugal Kishore Rai %A Sahariah, Biswajit %A Sakpal, Sushil S. %A Bar, Arun Kumar %A Bagchi, Sayan %A Sarma, Bani Kanta %X

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.

%B Organic letters %V 23 %P 7003-7007 %8 MAY %G eng %N 18 %9 Article %3

Foreign

%4 6.005 %R 10.1021/acs.orglett.1c00834