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Intramolecular hydrogen bonding of novel o ‐hydroxythioacetophenones and related compounds evaluated by deuterium isotope effects on 13 C chemical shifts
Author(s) -
Nguyen Trung Thanh,
Le Thach Ngoc,
Duus Fritz,
Hansen Bjarke K. V.,
Hansen Poul Erik
Publication year - 2007
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.1957
Subject(s) - chemistry , deuterium , kinetic isotope effect , intramolecular force , deuterium nmr , tautomer , hydrogen bond , chemical shift , reactivity (psychology) , hydrogen , carbon 13 nmr , isotope , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , molecule , medicine , physics , alternative medicine , quantum mechanics , pathology
A new class of compounds, the 2‐hydroxythioacetophenones, and related compounds have recently been synthesized. The hydrogen‐bond system has been characterized by NMR chemical shifts and deuterium isotope effects on these as well as by DFT calculations. Use of solid‐state 13 C NMR has enabled measurements of the intrinsic deuterium isotope effects of the most abundant tautomer of β‐thioxoketones. The compounds show very interesting long‐range deuterium isotope effects on the thiocarbonyl carbon. The intramolecular hydrogen bonds of o ‐hydroxythioacetophenones are found to be slightly stronger than those of the corresponding acetophenones. The reactivity and stability of the compounds can be related to hydrogen bonding and to the presence of electron donating substituents. Copyright © 2007 John Wiley & Sons, Ltd.