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Direct Spectroscopic Evidence of Hyperconjugation Unveils the Conformational Landscape of Hydrazides.

Authors :
Gloaguen, Eric
Brenner, Valérie
Alauddin, Mohammad
Tardivel, Benjamin
Mons, Michel
Zehnacker-Rentien, Anne
Declerck, Valérie
Aitken, David J.
Source :
Angewandte Chemie. Dec2014, Vol. 126 Issue 50, p13976-13979. 4p.
Publication Year :
2014

Abstract

The stereochemistry of hydrazides makes them especially interesting as building blocks for molecular design. An exhaustive conformational analysis of three model hydrazides was conducted in a conformer-selective approach by using a combination of high-level quantum chemistry calculations and vibrational spectroscopy in the gas phase and in solution. The NH stretch frequency was found to be highly sensitive to hyperconjugation, thus making it an efficient probe of the conformation of the neighboring nitrogen atom. This property greatly assisted the identification of the isomers observed experimentally in the conformer pool. A rationalization of the hydrazide conformational landscape is proposed, therefore paving the way for a better characterization of secondary structures in larger systems. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00448249
Volume :
126
Issue :
50
Database :
Academic Search Index
Journal :
Angewandte Chemie
Publication Type :
Academic Journal
Accession number :
99761056
Full Text :
https://doi.org/10.1002/ange.201407801