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Automated structure verification based on a combination of 1D 1 H NMR and 2D 1 H 13 C HSQC spectra
Author(s) -
Golotvin Sergey S.,
Vodopianov Eugene,
Pol Rostislav,
Lefebvre Brent A.,
Williams Antony J.,
Rutkowske Randy D.,
Spitzer Timothy D.
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.2034
Subject(s) - chemistry , heteronuclear single quantum coherence spectroscopy , spectrum (functional analysis) , two dimensional nuclear magnetic resonance spectroscopy , proton , nmr spectra database , spectral line , proton nmr , carbon 13 nmr satellite , nuclear magnetic resonance spectroscopy , chemical shift , nuclear magnetic resonance , crystallography , computational chemistry , stereochemistry , fluorine 19 nmr , physics , nuclear physics , quantum mechanics , astronomy
A method for structure validation based on the simultaneous analysis of a 1D 1 H NMR and 2D 1 H 13 C single‐bond correlation spectrum such as HSQC or HMQC is presented here. When compared with the validation of a structure by a 1D 1 H NMR spectrum alone, the advantage of including a 2D HSQC spectrum in structure validation is that it adds not only the information of 13 C shifts, but also which proton shifts they are directly coupled to, and an indication of which methylene protons are diastereotopic. The lack of corresponding peaks in the 2D spectrum that appear in the 1D 1 H spectrum, also gives a clear picture of which protons are attached to heteroatoms. For all these benefits, combined NMR verification was expected and found by all metrics to be superior to validation by 1D 1 H NMR alone. Using multiple real‐life data sets of chemical structures and the corresponding 1D and 2D data, it was possible to unambiguously identify at least 90% of the correct structures. As part of this test, challenging incorrect structures, mostly regioisomers, were also matched with each spectrum set. For these incorrect structures, the false positive rate was observed as low as 6%. Copyright © 2007 John Wiley & Sons, Ltd.