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Solution conformation and dynamics of L ‐6‐methylperhydroimidazo[1,5‐ c ]thiazole‐5,7‐dione (γ‐thiaprolinehydantoin). A 1 H and 13 C NMR study
Author(s) -
Borremans Frans A. M.,
Buděšínský Milos,
Callens Roland E. A.,
Anteunis Marc J. O.
Publication year - 1983
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/omr.1270210509
Subject(s) - chemistry , thiazolidine , thiazole , conformational isomerism , stereochemistry , vicinal , ring (chemistry) , nuclear magnetic resonance spectroscopy , crystallography , hydrogen bond , molecule , organic chemistry
The solution conformation of L‐6‐methylperhydroimidazo[1,5‐c]thiazole‐5,7‐dione (γ‐thiaprolinehydantoin) has been determined from an extensive 1 H and 13 C NMR study, allowing the extraction of vicinal inter‐proton and carbon‐hydrogen coupling constants. The major conformation of the thiazolidine ring is an envelope with C‐δ as the flap exo (δ − ). In solution the preferred solid state (twist) conformer with C‐α exo and C‐β endo ( α β T) is only a minor contributor. 13 C spin–lattice relaxation data reveal the flexibility of the thiazolidine ring.