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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Infrared Fingerprints of n(N) -> sigma{*}(NH) Hyperconjugation in Hydrazides

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Author(s):
Andrade, Laize A. F. [1] ; Silla, Josue M. [1] ; Cormanich, Rodrigo A. [2] ; Freitas, Matheus P. [1]
Total Authors: 4
Affiliation:
[1] Univ Fed Lavras, Dept Chem, BR-37200000 Lavras, MG - Brazil
[2] Univ Estadual Campinas, Inst Chem, POB 6154, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 2
Document type: Journal article
Source: Journal of Organic Chemistry; v. 82, n. 23, p. 12181-12187, DEC 1 2017.
Web of Science Citations: 2
Abstract

An earlier study demonstrated that hyperconjugation operates in hydrazides by analyzing the N-H stretching mode in gas phase infrared (IR) spectroscopy, and then observing two very distinct bands corresponding to isolated isomers experiencing or not the n(N) -> sigma{*}(N-H) electron delocalization. The present work reports a chemical method to obtain insight on the hyperconjugation in hydraiide derivatives from solution IR spectroscopy. The analogous amides did not show a v(N-H) red-shifted band, as the electron donor orbital in the above hyperconjugative interaction does not exist. In addition, the effect of electron withdrawing groups bonded to a nitrogen atom, namely the trifluoroacetyl and the methanesulfonyl groups, was analyzed on the conformational isomerism and on the ability to induce a stronger hyperconjugation in the resulting compounds. (AU)

FAPESP's process: 17/02364-0 - Mechanistic investigations of the biginelli reaction using experimental and theoretical approaches
Grantee:Rodrigo Antonio Cormanich
Support type: Scholarships abroad - Research