Evidence of an nN(amide) → π*Ar interaction in N-Alkyl-N,N′-diacylhydrazines
| Title | Evidence of an nN(amide) → π*Ar interaction in N-Alkyl-N,N′-diacylhydrazines |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Deka, JKishore Ra, Sahariah, B, Sakpal, SS, Bar, AKumar, Bagchi, S, Sarma, BKanta |
| Journal | Organic letters |
| Volume | 23 |
| Issue | 18 |
| Pagination | 7003-7007 |
| Date Published | MAY |
| Type of Article | Article |
| ISSN | 1523-7060 |
| 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. |
| DOI | 10.1021/acs.orglett.1c00834 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.005 |
Divison category:
Physical and Materials Chemistry