Benzo[b]Phenanthro[4,3-d]Thiophene: Spectral Assignment by two-dimensional NMR Methods and Tertiary Structure Determination

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Journal Title, Volume, Page: 
Magnetic Resonance in Chemistry Volume 24, Issue 12, pages 1039–1043, December 1986
Year of Publication: 
1986
Authors: 
M. J. Musmar
Department of Medicinal Chemistry, College of Pharmacy, University of Houston—University Park, Houston, Texas 77004, USA
Current Affiliation: 
Department of Pharmacy, Faculty of Medicine and Health Sciences, An-Najah National University, Nablus, Palestine
Andrew S. Zektzer
Department of Medicinal Chemistry, College of Pharmacy, University of Houston—University Park, Houston, Texas 77004, USA
Gary E. Martin
Department of Medicinal Chemistry, College of Pharmacy, University of Houston—University Park, Houston, Texas 77004, USA
Robert T. Gampe Jr.
Drug Discovery Group, Abbott Laboratories, Abbott Park, Illinois 60064, USA
Milton L. Lee
Department of Chemistry, Brigham Young University, Provo, Utah 84602, USA
Marvin L. Tedjamulia
Department of Chemistry, University of South Florida, Tampa, Florida 33620, USA
Raymond N. Castle
Department of Chemistry, University of South Florida, Tampa, Florida 33620, USA
Ralph E. Hurd
General Electric NMR Instruments, 255 Fourier Avenue, Fremont, California 94539, USA
Preferred Abstract (Original): 

Two-dimensional heteronuclear chemical shift correlation, heteronuclear relayed coherence transfer and autocorrelated 13C—13C double quantum coherence have been used to assign the proton and 13C NMR spectra of benzo[b]phenanthro[4,3-d]thiophene. The highly complementary nature of the heteronuclear relay and carbon–carbon double quantum spectra conveniently provides the means of avoiding breaks in the carbon–carbon connectivity network assembled by the latter, which may arise when strongly AB rather than AX carbon–carbon pairings are encountered. Nuclear Overhauser difference spectra have shown the title compound to possess a tertiary helical structure similar to that of phenanthro[3,4-b]thiophene; the average separation between the H-1 and H-13 atoms of the title compound was found to be 2.06 ± 0.04 Å.

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