skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Assignment of 1 H and 13 C NMR data for three pairs of diastereomers of 4′-X benzo[1,3]cyclopropa[1,2- b ]chromene-4,5-diones (X = H, OCH 3 , and Cl)

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [2]
  1. Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro Portugal
  2. Instituto de Química Médica (IQM-CSIC), Juan de la Cierva, 3 E-28006 Madrid Spain
Publication Date:
Sponsoring Org.:
USDOE Office of Nuclear Energy (NE), Nuclear Fuel Cycle and Supply Chain
OSTI Identifier:
1529636
Grant/Contract Number:  
SFRH/BD/76407/2011; FCT UID/QUI/00062/2013
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Magnetic Resonance in Chemistry
Additional Journal Information:
Journal Name: Magnetic Resonance in Chemistry Journal Volume: 57 Journal Issue: 8; Journal ID: ISSN 0749-1581
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Sousa, Joana L. C., Silva, Artur M. S., Alkorta, Ibon, and Elguero, José. Assignment of 1 H and 13 C NMR data for three pairs of diastereomers of 4′-X benzo[1,3]cyclopropa[1,2- b ]chromene-4,5-diones (X = H, OCH 3 , and Cl). United Kingdom: N. p., 2019. Web. doi:10.1002/mrc.4892.
Sousa, Joana L. C., Silva, Artur M. S., Alkorta, Ibon, & Elguero, José. Assignment of 1 H and 13 C NMR data for three pairs of diastereomers of 4′-X benzo[1,3]cyclopropa[1,2- b ]chromene-4,5-diones (X = H, OCH 3 , and Cl). United Kingdom. doi:10.1002/mrc.4892.
Sousa, Joana L. C., Silva, Artur M. S., Alkorta, Ibon, and Elguero, José. Wed . "Assignment of 1 H and 13 C NMR data for three pairs of diastereomers of 4′-X benzo[1,3]cyclopropa[1,2- b ]chromene-4,5-diones (X = H, OCH 3 , and Cl)". United Kingdom. doi:10.1002/mrc.4892.
@article{osti_1529636,
title = {Assignment of 1 H and 13 C NMR data for three pairs of diastereomers of 4′-X benzo[1,3]cyclopropa[1,2- b ]chromene-4,5-diones (X = H, OCH 3 , and Cl)},
author = {Sousa, Joana L. C. and Silva, Artur M. S. and Alkorta, Ibon and Elguero, José},
abstractNote = {},
doi = {10.1002/mrc.4892},
journal = {Magnetic Resonance in Chemistry},
number = 8,
volume = 57,
place = {United Kingdom},
year = {2019},
month = {6}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1002/mrc.4892

Citation Metrics:
Cited by: 2 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Density‐functional thermochemistry. III. The role of exact exchange
journal, April 1993

  • Becke, Axel D.
  • The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652
  • DOI: 10.1063/1.464913

Synthesis, 1H and 13C NMR Study of Pyrazoles Derived from Chiral Cyclohexanones (3-Methylcyclohexanone, Menthone, Pulegone, Dihydrocarvone and Carvone)
journal, January 2002

  • Hafez Hussien Elghandour, Ahmed; Faure, Robert; Frideling, Aline
  • HETEROCYCLES, Vol. 57, Issue 2
  • DOI: 10.3987/COM-01-9407

19F‐NMR Diastereotopic Signals in Two N-CHF2 Derivatives of (4S,7R)-7,8,8-Trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole
journal, November 2017


The structure of azines derived from C -formyl-1 H -imidazoles in solution and in the solid state: tautomerism, configurational and conformational studies : Azines derived from
journal, February 2013

  • Pinto, Joana; Silva, Vera L. M.; Silva, Artur M. S.
  • Magnetic Resonance in Chemistry, Vol. 51, Issue 4
  • DOI: 10.1002/mrc.3926

J -Based Analysis and DFT-NMR Assignments of Natural Complex Molecules: Application to 3β,7-Dihydroxy-5,6-epoxycholestanes
journal, August 2008

  • Poza, Jesús Javier; Jiménez, Carlos; Rodríguez, Jaime
  • European Journal of Organic Chemistry, Vol. 2008, Issue 23
  • DOI: 10.1002/ejoc.200800358

Assigning the Stereochemistry of Pairs of Diastereoisomers Using GIAO NMR Shift Calculation
journal, June 2009

  • Smith, Steven G.; Goodman, Jonathan M.
  • The Journal of Organic Chemistry, Vol. 74, Issue 12
  • DOI: 10.1021/jo900408d

Beyond DP4: an Improved Probability for the Stereochemical Assignment of Isomeric Compounds using Quantum Chemical Calculations of NMR Shifts
journal, December 2015

  • Grimblat, Nicolás; Zanardi, María M.; Sarotti, Ariel M.
  • The Journal of Organic Chemistry, Vol. 80, Issue 24
  • DOI: 10.1021/acs.joc.5b02396

Density-functional exchange-energy approximation with correct asymptotic behavior
journal, September 1988


Direct Investigation of Halogen Bonds by Solid-State Multinuclear Magnetic Resonance Spectroscopy and Molecular Orbital Analysis
journal, May 2014

  • Viger-Gravel, Jasmine; Leclerc, Sophie; Korobkov, Ilia
  • Journal of the American Chemical Society, Vol. 136, Issue 19
  • DOI: 10.1021/ja5013239

Assigning Stereochemistry to Single Diastereoisomers by GIAO NMR Calculation: The DP4 Probability
journal, September 2010

  • Smith, Steven G.; Goodman, Jonathan M.
  • Journal of the American Chemical Society, Vol. 132, Issue 37
  • DOI: 10.1021/ja105035r

Calculated Chemical Shifts as a Fine Tool of Conformational Analysis: An Unambiguous Solution for Haouamine Alkaloids
journal, August 2008

  • Belostotskii, Anatoly M.
  • The Journal of Organic Chemistry, Vol. 73, Issue 15
  • DOI: 10.1021/jo702766x

Self‐Consistent Molecular‐Orbital Methods. IX. An Extended Gaussian‐Type Basis for Molecular‐Orbital Studies of Organic Molecules
journal, January 1971

  • Ditchfield, R.; Hehre, W. J.; Pople, J. A.
  • The Journal of Chemical Physics, Vol. 54, Issue 2
  • DOI: 10.1063/1.1674902

Molecular orbital calculations of hydrogen-hydrogen coupling constants in substituted cyclopropanes
journal, January 1971


Observation of Diastereotopic Signals in 15 N NMR Spectroscopy
journal, February 2015

  • Alkorta, Ibon; Dardonville, Christophe; Elguero, José
  • Angewandte Chemie International Edition, Vol. 54, Issue 13
  • DOI: 10.1002/anie.201412144

A computational study of the effect of C-lithiation on the NMR properties (chemical shifts and coupling constants) of aziridines
journal, August 2008


Pyrazolo[1,5-a]pyrimidines. A combined multinuclear magnetic resonance (1H,13C,15N,19F) and DFT approach to their structural assignment
journal, June 2007

  • Sanz, Dionisia; Claramunt, Rosa M.; Saini, Anil
  • Magnetic Resonance in Chemistry, Vol. 45, Issue 6
  • DOI: 10.1002/mrc.1992

Halogen effect on structure and 13 C NMR chemical shift of 3,6-disubstituted- N -alkyl carbazoles
journal, August 2013

  • Radula-Janik, Klaudia; Kupka, Teobald; Ejsmont, Krzysztof
  • Magnetic Resonance in Chemistry, Vol. 51, Issue 10
  • DOI: 10.1002/mrc.3992

Self‐consistent molecular orbital methods 25. Supplementary functions for Gaussian basis sets
journal, April 1984

  • Frisch, Michael J.; Pople, John A.; Binkley, J. Stephen
  • The Journal of Chemical Physics, Vol. 80, Issue 7
  • DOI: 10.1063/1.447079

A guide to small-molecule structure assignment through computation of (1H and 13C) NMR chemical shifts
journal, February 2014

  • Willoughby, Patrick H.; Jansma, Matthew J.; Hoye, Thomas R.
  • Nature Protocols, Vol. 9, Issue 3
  • DOI: 10.1038/nprot.2014.042

Théorie quantique des courants interatomiques dans les combinaisons aromatiques
journal, January 1937


Statistical analysis of13C and15N NMR chemical shifts from GIAO/B3LYP/6-311 + + G** calculated absolute shieldings
journal, January 2007

  • Blanco, Fernando; Alkorta, Ibon; Elguero, José
  • Magnetic Resonance in Chemistry, Vol. 45, Issue 9
  • DOI: 10.1002/mrc.2053

A theoretical and NMR experimental study of N1,N3-di(3-aminoacridin-6-yl)-isophthalamide and N2,N6-di(3-aminoacridin-6-yl)-2,6-dicarboxamide
journal, June 2009


Experimental measurements and theoretical calculations of the chemical shifts and coupling constants of three azines (benzalazine, acetophenoneazine and cinnamaldazine)
journal, September 2008

  • Silva, Artur M. S.; Sousa, Regina M. S.; Jimeno, María Luisa
  • Magnetic Resonance in Chemistry, Vol. 46, Issue 9
  • DOI: 10.1002/mrc.2272

A theoretical and experimental NMR study of (+)-biotin methyl ester
journal, February 2009

  • Santa María, Dolores; Claramunt, Rosa M.; Herranz, Fernando
  • Journal of Molecular Structure, Vol. 920, Issue 1-3
  • DOI: 10.1016/j.molstruc.2008.11.027

Ab initio hybrid DFT–GIAO calculations of the shielding produced by carbon–carbon bonds and aromatic rings in 1H NMR spectroscopy
journal, January 1998

  • Alkorta, Ibon; Elguero, Jose´
  • New Journal of Chemistry, Vol. 22, Issue 4
  • DOI: 10.1039/a708743h

An experimental and theoretical NMR study of NH-benzimidazoles in solution and in the solid state: proton transfer and tautomerism
journal, January 2014

  • Nieto, Carla I.; Cabildo, Pilar; García, M. Ángeles
  • Beilstein Journal of Organic Chemistry, Vol. 10
  • DOI: 10.3762/bjoc.10.168