Carbon-13 nuclear magnetic resonance studies of (Z)-5-fluoro-2-methyl-1-{[p-(methylsulfinyl)phenyl] methylene}-1H-indene-3-acetic acid (sulindac) and some related compounds

1978 ◽  
Vol 56 (16) ◽  
pp. 2129-2133 ◽  
Author(s):  
Alan Wilmot Douglas
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Acetic Acid ◽  
Magnetic Resonance ◽  
Nuclear Spin ◽  
Substituent Effects ◽  
Coupling Constants ◽  
Spin Coupling ◽  
Nuclear Magnetic Resonance Spectra ◽  
Spin Coupling Constants ◽  
Nuclear Magnetic

Carbon-13 nuclear magnetic resonance spectra have been obtained and fully assignee for a number of 2-methyl-1-{[p-(methylthio) or -(methylsulfinyl}phenyl]methylene}-1H-indene-3- acetic acid derivatives, including the potent anti-inflammatory compound sulindac, 1Z. Paired E and Z isomers were studied along with the sulindac sodium salt and ethyl ester in the Z series. Variations in steric crowding in E vs. Z isomers produce chemical shift effects which alternate with the number of intervening bonds. Fluorine substituent effects and 19F nuclear spin coupling to 13C nuclei, second-order features in off-resonance proton-decoupled spectra, and values of long-range 13CH nuclear spin coupling constants have been employed in making a complete set of assignments.

THE ANALYSIS OF NUCLEAR MAGNETIC RESONANCE SPECTRA: I. SYSTEMS OF TWO AND THREE NUCLEI

1957 ◽  
Vol 35 (1) ◽  
pp. 67-83 ◽  
Author(s):  
H. J. Bernstein ◽  
J. A. Pople ◽  
W. G. Schneider
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Coupling Constants ◽  
Spin Coupling ◽  
Resonance Signal ◽  
Nuclear Magnetic Resonance Spectra ◽  
Order Of Magnitude ◽  
Spin Coupling Constants ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

This paper is concerned with the general problem of the interpretation and analysis of nuclear magnetic resonance spectra of systems in which chemical shift and spin-coupling constants are of the same order of magnitude. Only nuclei of spin 1/2 are considered. Detailed methods are developed for:(a) Two chemically non-equivalent nuclei of the same species (written AB),(b) Three nuclei of the same species, two of which are equivalent (written AB2),(c) Three nuclei (ABX), two of which are of the same species (AB) and the third (X) is either a different species or has a resonance signal well separated from A and B.Proton resonance spectra of S-guaiazulene, 2,6-lutidine, and 2,3-lutidine are reported and used as examples of the methods of analysis.

High-resolution nuclear-magnetic-resonance spectra of hydrocarbon groupings I. Some dichloro-propenes

1959 ◽  
Vol 252 (1271) ◽  
pp. 488-505 ◽  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
High Resolution ◽  
Resonance Spectrum ◽  
Coupling Constants ◽  
Spin Coupling ◽  
Nuclear Magnetic Resonance Spectra ◽  
Spin Coupling Constants ◽  
Spin Spin Coupling ◽  
Nuclear Magnetic

An analysis has been made of the high-resolution nuclear-magnetic-resonance spectrum given by the hydrogen nuclei of 2:3-dichloropropene-l and cisand trans 1:3-dichloropropene-1. The spectra at 40 Mc/s of the 1:3-dichloropropenes were analyzed by means of the theory for ABX 2 developed here; the 16·2 Mc/s spectra were analyzed according to the ABC 2 theory by means of a digital computer. It is concluded that the ‘long-range’ spin-spin coupling constants between hydrogen nuclei on carbon atoms 1 and 3 of the 1 : 3-dichloropropenes are of opposite sign to the remainder. A correlation of these results with earlier work on butene-1 by Alexander (1958) leads to analogous conclusions for this molecule also.

THE ANALYSIS OF NUCLEAR MAGNETIC RESONANCE SPECTRA: III. PYRIDINE AND DEUTERATED PYRIDINES

1957 ◽  
Vol 35 (12) ◽  
pp. 1487-1495 ◽  
Author(s):  
W. G. Schneider ◽  
H. J. Bernstein ◽  
J. A. Pople
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
High Resolution ◽  
Chemical Shifts ◽  
Coupling Constants ◽  
Spin Coupling ◽  
Calculated Spectrum ◽  
Proton Resonance ◽  
Nuclear Magnetic Resonance Spectra ◽  
Spin Coupling Constants

The proton resonance spectra of pyridine, 2,6-pyridine-d2, 3-pyridine-d1, and 4-pyridine-d1 have been obtained for the pure liquids under conditions of high resolution. The spectra have been analyzed as proton groupings of AB2X2, AB2, perturbed ABX, and B2X2 respectively. The spin-coupling constants obtained from analysis of the simpler spectra of the deuterated molecules were used to suggest trial solutions for the analysis of the complicated AB2X2 spectrum of pyridine. A final set of chemical shifts and spin-coupling constants derived for pyridine give satisfactory agreement between the observed and calculated spectrum.

Sign in / Sign up

Export Citation Format

Share Document