An ideal one-dimensional antiferromagnetic spin system observed in hydrogen-bonded naphth[2,3-d]imidazol-2-yl nitronyl nitroxide crystal: The role of the hydrogen bond

Journal of Physical Chemistry B

Volumn 108, Issue 20, 2004, Pages 6144-6151

  Nagashima, Hideaki ^a   Inoue, Hidenari ^a   Yoshioka, Naoki ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFERROMAGNETISM; AROMATIC COMPOUNDS; CRYSTAL STRUCTURE; DEUTERIUM; HYDROGEN BONDS; INFRARED SPECTROSCOPY; PARAMAGNETIC RESONANCE; PROTONS; X RAY ANALYSIS;

BULK MAGNETISM; CRYSTAL SCAFFOLDING; MAGNETIC PATHWAY INTERACTION; NITRONYL NITROXIDE (NN);

CRYSTALS;

EID: 2642529616     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp035849r     Document Type: Article

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43. We calculated spin densities and Fermi contact terms of 2 and phenyl nitronyl nitroxide at the UB3LYP/6-31G*//AM1 level, by changing the dihedral angle between the aryl rings and the ONCNO moieties from 0° to 90°. Calculations for 2 show that the sign of the spin densities at the NH proton changes while changing the angle, although that of Fermi contacts is always positive. On the other hand, the sign of both the spin densities and Fermi contact terms of the ortho-proton of phenyl nitronyl nitroxide is always positive. In the case of 2, the magnitude of spin density induced through a covalent bond seems smaller than that induced through an intramolecular hydrogen bond. Therefore, we consider that the explanation is reasonable for imidazol-2-yl nitronyl nitroxide derivatives. See Supporting Information (Figure IS) for more details.
44. We investigated the angular dependence of the calculated J values for a hydrogen-bonded dimeric coordinate of 4 by rotating the naphthimidazole ring or NN unit around the C-C bond, from -30° to +30° (0° corresponds to the experimental geometry). The rotation of the naphthimidazole ring does not affect the J values very much, whereas rotation of the NN unit does affect the J values significantly, showing that the close contact between the nitroxide O atoms induced by the intermolecular hydrogen bond, rather than the intermolecular NH...ON hydrogen bond, is responsible for the antiferromagnetic character. In Figure 2S in the Supporting Information, the maximum J value appears at 0°, which implies that the NH...ON hydrogen bond is a ferromagnetic interaction pathway. See Supporting Information (Figures 2S and 3S) for more details.
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