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The Structure of N 1 ‐Hydroxylophine N 3 ‐Oxide (=1‐Hydroxy‐2,4,5‐ triphenyl‐1 H ‐imidazole 3‐Oxide) in the Solid State
Author(s) -
SánchezMigallón Ana,
de la Hoz Antonio,
López Concepción,
Claramunt Rosa M.,
Infantes Lourdes,
Motherwell Sam,
Shankland Kenneth,
Nowell Harriott,
Alkorta Ibon,
Elguero José
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390091
Subject(s) - chemistry , imidazole , crystallography , oxide , hydrogen bond , molecule , proton , crystal structure , nuclear magnetic resonance spectroscopy , spectroscopy , stereochemistry , organic chemistry , physics , quantum mechanics
The crystal structure of 1‐hydroxy‐2,4,5‐triphenyl‐1 H ‐imidazole 3‐oxide ( 1 ) has been determined from laboratory X‐ray powder‐diffraction data. The two independent molecules in the asymmetric unit form chains via OH⋅⋅⋅O hydrogen bonds related by a twofold screw axis. One of the O⋅⋅⋅O distances is extremely short (2.32(1) and 2.43(1) Å). Solid‐state NMR spectroscopy (CPMAS) combined with calculation of absolute shieldings (GIAO/B3LYP/6‐31G*) allowed us to determine that the compound behaves as if the OH⋅⋅⋅O hydrogen bond has the proton in the middle (single‐well potential), resulting in the near identity of both 15 N‐NMR signals.