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Comparative analysis of NMR spectral parameters and molecular dynamics of 1:6‐anhydro‐3:4‐thia‐2‐ O ‐tosyl‐β‐ D ‐allopyranose and 1,6:3,4‐dianhydro‐2‐ O ‐tosyl‐β‐ D ‐galactopyranose in the solid phase
Author(s) -
Potrzebowski Marek J.,
Kaźmierski Sławomir,
Olejniczak Sebastian,
Heliński Jan,
Ciesielski Włodzimierz,
Dőlle Andreas
Publication year - 2005
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.906
Subject(s) - chemistry , tosyl , intermolecular force , hydrogen bond , carbon 13 nmr , relaxation (psychology) , molecular dynamics , computational chemistry , chemical shift , crystallography , stereochemistry , analytical chemistry (journal) , molecule , organic chemistry , psychology , social psychology
A search of x‐ray data for 1:6‐anhydro‐3:4‐thia‐2‐ O ‐tosyl‐β‐ D ‐allopyranose ( 1 ) and 1:6,3:4‐dianhydro‐2‐ O ‐tosyl‐β‐ D ‐galactopyranose ( 2 ) revealed two CH·O intermolecular contacts for both compounds and one CH·S interaction for 1 . Inspection of hydrogen bonding showed that these interactions are stronger for 2 . The 13 C relaxation times in the rotating frame, 13 C T * 1ρ , measured at B 1 =36.7 kHz showed apparent differences in internal molecular motion on the kilohertz scale for both samples. A PASS‐2D experiment recorded at a spinning rate of 1 kHz was performed to establish the values of principal elements of chemical shift tensors 13 C δ ii . DFT GIAO calculations of shielding parameters were carried out and the orientations of 13 C δ ii were assigned. An attempt to correlate 13 C NMR spectral parameters and molecular dynamics in the solid state with structure, internal motion and intermolecular interactions is presented. Copyright © 2005 John Wiley & Sons, Ltd.