Differences between gas-phase and solid state molecular structures of the simplest phosphonium ylide, Me3P=CH2

Angewandte Chemie - International Edition

Volumn 37, Issue 12, 1998, Pages 1670-1672

  Mitzel, Norbert W ^a   Brown, Daniel H ^b   Parsons, Simon ^b   Brain, Paul T ^b   Pulham, Colin R ^b   Rankin, David W H ^b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

Ab initio calculations; Electron diffraction; Structure elucidation; Ylides

Indexed keywords

EID: 0032479496     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980703)37:12<1670::AID-ANIE1670>3.0.CO;2-S     Document Type: Article

References (15)

1. H.-J. Bestmann, R. Zimmermann, Methoden der Organischen Chemie (Houben-Weyl-Mülter), 1982, Vol. E1.
2. A. W. Johnson, Ylides and imines of phosphorus, John Wiley, New York, 1993.
3. H. Schmidbaur, W. Tronich, Chem. Ber. 1968, 101, 595-603.
4. E. A. V. Ebsworth, T. E. Fraser, D. W. H. Rankin, Chem. Ber. 1977, 110, 3594-3500.
5. a) N. W. Mitzel, B. A. Smart, A. J. Blake, H. E. Robertson, D. W. H. Rankin, J. Chem. Phys. 1996, 100, 9339-9347.
6. b) A. J. Blake, P.T. Brain, H. McNab, J. Miller, C. A. Morrison, S. Parsons, D. W. H. Rankin, H. E. Robertson, B. A. Smart, J. Chem. Phys. 1996, 100, 12280-12287.
7. a) Molecular Structure by Diffraction Methods, Specialist Periodical Reports, The Chemical Society, 1975, p. 72;
8. b) V. J. Klimkowski, J. D. Ewbank, C. Van Alsenoy, J. N. Scarsdale, L. Schäfer, J. Am. Chem. Soc. 1982, 104, 1476-1480.
9. 2 group refines the structure with a significantly higher Rg.
10. This parameter is mainly the result of restraints in the GED analysis and thus represents almost pure theoretical information.
11. H. Schmidhaur, J. Jeong, A. Schier, W. Graf, D. L. Wilkinson, G. Müller, New J. Chem. 1989, 13, 341-352.
12. N. W. Mitzel, B. A. Smart, K.-H. Dreihäupl, D. W. H. Rankin, H. Schmidbaur, J. Am. Chem. Soc. 1996, 118, 12673-12682.
13. -1. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100730. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ (Fax: (+44)(1223)-336-033; e-mail: deposit@ccdc.cam.ac.uk).
14. -1. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100730. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ (Fax: (+44)(1223)-336-033; e-mail: deposit@ccdc.cam.ac.uk).
15. 2 unit (Figure 3c), as the model suggests both H-positions are clearly off the mirror plane of the disordered heavy-atom skeleton. We are grateful to Prof. R. Boese and the other referees of this paper, who drew our attention to these disorder models, which clearly needed to be considered before drawing the conclusions outlined in this paper.