Utilization of a Modified Version of the Technique as an Adjunct in the Total Assignment of the 'H- and "C-NMR Spectra of the Mutagen Phenanthro[3,4-b]thiophene
Department of Medicinal chemistry, Collage of pharmacy, University of Houston, Houston, Texas 77004
Grey E. Martin
Department of Medicinal chemistry, Collage of pharmacy, University of Houston, Houston, Texas 77004
Preferred Abstract (Original):
Development of successively
higher field nmr spectrometers has facilitated the study of increasingly more
complex molecules, although smaller molecules such as
phenanthro[3,4-b]thiophene still offer very substantial assignment problems
because of the highly congested nature of t1leir 'H- and "C-nmr spectra.
Assignments of such spectra, if they are to be unequivocal, frequently require
the utilization of two-dimensional nmr spectroscopic techniques. Total
assignments of the 'H- and "C-nmr spectra of phenanthro[3,4-b]thiophene
are reported. Assignments were based on a conventional high resolution 500 MHz
'H-nmr spectrum, autocorrelated two-dimensional 'H-nmr spectra (COSY),
two-dimensional 'H-"C chemical shift correlation spectra and a modified
version of autocorrelated "C-"C double quantum coherence
two-dimensional nmr spectroscopy. From NOE measurements, a separation of 1.99 A
between H1 and HII was computed, suggesting that phenanthro[3,4-b]thiophene
has a pronounced helical conformation in solution.