03974nas a2200205 4500008004100000022001400041245008600055210007400141260000800215300001400223490000700237520326500244100002803509700002303537700002303560700002103583700001803604700002303622856012303645 2021 eng d a1523-706000aEvidence of an nN(amide) → π*Ar interaction in N-Alkyl-N,N′-diacylhydrazines0 aEvidence of an nNamide → πAr interaction in NAlkylNN′diacylhydra cMAY a7003-70070 v233 a
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.
1 aDeka, Jugal, Kishore Ra1 aSahariah, Biswajit1 aSakpal, Sushil, S.1 aBar, Arun, Kumar1 aBagchi, Sayan1 aSarma, Bani, Kanta uhttp://library.ncl.res.in/content/evidence-nnamide-%E2%86%92-%CF%80ar-interaction-n-alkyl-nn%E2%80%B2-diacylhydrazines