Structural evidence for resonance-assisted O–H···S hydrogen bonding

Abstract

By far the shortest hydrogen bonds of the O–H···S type occur in monothio-ß-diketones and related substances (H···S distances 1.9–2.0 Å); it is shown with crystal correlation techniques that this very short hydrogen bonding is facilitated by resonance assistance similar to that occurring in the oxygen analogues.

References

1. F. H. Allen, C. M. Bird, R. S. Rowland and P. R. Raithby, Acta Crystallogr., Sect. B, 1997, 53, 680; 1997, 53, 596.
2. F. H. Allen and O. Kennard, Chem. Des. Autom. News, 1993, 8, 1.
3. L. F. Power, K. E. Turner and F. H. Moore, J. Chem. Soc., Perkin Trans. 2, 1976, 249.
4. T. Steiner and W. Saenger, Acta Crystallogr., Sect. B, 1994, 50, 348.
5. V. Bertolasi, P. Gilli, V. Ferretti and G. Gilli, Chem. Eur. J., 1996, 2, 925.
6. E. Steinwender and W. Mikenda, Montash. Chem., 1990, 121, 809.
7. G. Gilli, F. Bellucci, V. Ferretti and P. Gilli, J. Am. Chem. Soc., 1989, 111, 1023.
8. P. Gilli, V. Bertolasi, V. Ferretti and G. Gilli, J. Am. Chem. Soc., 1994, 116, 909.
9. V. Bertolasi, P. Gilli, V. Ferretti and G. Gilli, Acta Crystallogr., Sect. B, 1994, 50, 617.
10. T. Steiner, Chem. Commun., 1997, 727.