The crystal structure of 2-(chloromethyl)-5-(phthalimidomethyl)thiophene (1), as an example of a 2,5-disubstituted thiophene, together with data from semi-empirical and ab initio calculations provide strong evidence against an intramolecular S ⋯ N attraction in 2-formylthiophene semicarbazone (2), as well as in other five-membered heterocycles.
G. Lugert, J. Manero, M. Feigel and M. Bremer, J. Chem. Soc., Chem. Commun., 1988, 1395 DOI: 10.1039/C39880001395
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