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Real‐time mechanistic monitoring of an acetal hydrolysis using ultrafast 2D NMR
Author(s) -
Queiroz Luiz H. K.,
Giraudeau Patrick,
dos Santos Fabiane A. B.,
Oliveira Kleber T.,
Ferreira Antonio G.
Publication year - 2012
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.3827
Subject(s) - chemistry , acetal , heteronuclear single quantum coherence spectroscopy , hemiacetal , hydrolysis , computational chemistry , carbon 13 nmr , ultrashort pulse , proton nmr , nuclear magnetic resonance spectroscopy , organic chemistry , laser , physics , optics
Ultrafast (UF) 2D NMR makes it possible to obtain a 2D NMR spectrum in less than a second. Here, UF‐HSQC experiments are used for the real‐time mechanistic study of an acetal hydrolysis at ¹³C natural abundance, and it is possible to characterize the presence of the hemiacetal, an intermediate with a well‐known short lifetime. The assignments are confirmed and rationalized by quantum calculations of ¹H and ¹³C NMR chemical shifts and natural bonding orbital analysis. Copyright © 2012 John Wiley & Sons, Ltd.