✦ LIBER ✦

The Structure of N1-Hydroxylophine N3-Oxide (=1-Hydroxy-2,4,5- triphenyl-1H-imidazole 3-Oxide) in the Solid State

✍ Scribed by Ana Sánchez-Migallón; Antonio de la Hoz; Concepción López; Rosa M. Claramunt; Lourdes Infantes; Sam Motherwell; Kenneth Shankland; Harriott Nowell; Ibon Alkorta; José Elguero

Publisher: John Wiley and Sons
Year: 2003
Tongue: German
Weight: 178 KB
Volume: 86
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200390091

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✦ Synopsis

Abstract

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 OH⋅⋅⋅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 OH⋅⋅⋅O hydrogen bond has the proton in the middle (single‐well potential), resulting in the near identity of both ^15^N‐NMR signals.

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