Concomitant Conformational Polymorphism: Mechanochemical Reactivity and Phase Relationships in the (Methanol)cis-dioxo(N-salicylidene-2-amino-3-hydroxypyridine)molybdenum(VI) TrimorphClick to copy article linkArticle link copied!
Abstract
The title compound, [MoO2(L)(CH3OH)], crystallizes as a concomitant conformational trimorph. The occurrence domains, under which these forms can be prepared, separated, and/or interconverted, were explored and determined in terms of the crystallization conditions and solid-state reactions. Solvent-free reactions resulted in dissociation of coordinated methanol, producing two new complexes, monomeric [MoO2(L)] and polymeric [MoO2(L)]n. They both bind methanol molecule from its vapor, thus providing a pure α-form of the title complex. All forms have been characterized and compared to each other by a variety of methods including elemental analysis, Fourier transform IR, thermal methods, X-ray powder diffraction, and single-crystal X-ray structure determination.
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(49)
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(12)
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(41)
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(14)
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(41)
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(73)
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(18)
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(16)
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(8)
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