Gas Electron Diffraction Study of the Molecular Structure of Di-2-pyridyl Sulphide

Conformational energy contour maps of the six isomers of oxybispyridine have been constructed using the ab initio STO‐3G molecular orbital method. The calculations (employing a partial rigid rotor) for all six isomers indicate that the minimum energy conformers are not planar and that energy barriers between 70–1000 kJ mol−1 restrict interconversion to planar structures, thereby preventing conjugation between the p‐electrons of the oxygen atom with the π system of the pyridine rings. It is postulated that of the three mechanisms used to explain conformer interconversion about the CO bond, the disrotatory one‐ring flip mechanism is the most appropriate, since the “Morino's” structures are all within 2.5 kJ mol−1 of the minimum. Furthermore, room temperature accessibility of the “Morino's” structures suggests that the Smiles rearrangement would be possible for suitably substituted derivatives of these isomers.

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Gas Electron Diffraction Study of the Molecular Structure of Di-2-pyridyl Sulphide

Abstract: The gas-phase electron diffraction study of di-2-pyridyl sulphide has yielded r

Cited by 8 publications

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ChemInform Abstract: GAS ELECTRON DIFFRACTION STUDY OF THE MOLECULAR STRUCTURE OF DI‐2‐PYRIDYL SULFIDE

ChemInform Abstract: GAS ELECTRON DIFFRACTION STUDY OF THE MOLECULAR STRUCTURE OF DI‐2‐PYRIDYL SULFIDE

Oxybispyridines, thiobispyridines and selenobispyridines

A conformational analysis of the six isomers of oxybispyridine

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