Natural bond orbital rationalizations of NMR observations for metal-ligand bonding (II): Rehybridization of phosphorus arising from coordination of methyl-phenyl-phosphines

Journal of the Chinese Chemical Society

Volumn 58, Issue 2, 2011, Pages 163-173

  Su, Wei Lin ^a   Huang, Hsiu Ping ^a   Chen, Wei Ting ^a   Hsu, Wen Yi ^a   Chang, Hsi Yen ^a   Ho, Szu Yu ^a   Wang, Shao Pin ^b   Shyu, Shin Guang ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

^b INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

Methyl phenyl phosphines; Natural bond orbital (NBO) analysis; NMR spin lattice relaxation times; Rehybridization of phosphorus lone pair

Indexed keywords

EID: 79955537184     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.201190072     Document Type: Article

References (40)

1. Wang, S. P.; Yuan, P.; Schwartz, M. Inorg. Chem. 1990, 29, 484-487.
2. Wang, S. P.; Richmond, M. G.; Schwartz, M. J. Am. Chem. Soc. 1992, 114, 7595-7596.
3. Wang, K. S.;Wang, D.; Yang, K.; Richmond, M. G.; Schwartz, M. Inorg. Chem. 1995, 34, 3241-3244.
4. Weinhold, F.; Landis, C. R. Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective; Cambridge University Press: United Kingdom, 2005; Sections 3.5, 4.6.
5. Wang, S. P.; Yan, K.M.; Hsu,W. Y.; Huang, M. Y.;Wu, M. Y. J. Chin. Chem. Soc. 2009, 56, 1205-1215.
6. Lukehart, C. M. Fundamental Transition Metal Organometallic Chemistry; Brooks/Cole Publishing Co.: Monterey, CA, 1985.
7. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
8. Angelici, R. J.; Malone, M. D. Inorg. Chem. 1967, 6, 1731-1736.
9. Golovin, M. N.; Rahman, Md. M.; Belmonte, J. E.; Giering, W. P. Organometallics 1985, 4, 1981-1991.
10. Rahman, Md. M.; Liu, H.-Y.; Prock, A.; Giering, W. P. Organometallics 1987, 6, 650-658.
11. Rahman, Md. M.; Liu, H.-Y.; Eriks, K.; Prock, A.; Giering, W. P. Organometallics 1989, 8, 1-7.
12. Liu, H.-Y.; Eriks, K.; Prock, A.; Giering, W. P. Organometallics 1990, 9, 1758-1766.
13. Orpen, A. G.; Connelly, N. G. J. Chem. Soc. Chem. Commun. 1985, 1310-1311.
14. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211-7218.
15. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066-4073.
16. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.
17. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736-1740.
18. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
19. Carpenter, J. E.;Weinhold, F. J. Mol. Struct. (Theochem) 1988, 169, 41-62.
20. Weinhold. F.; Carpenter, J. E. In The Structure of Small Molecules and Ions; Naaman, R.; Vager, Z., Eds.; Plenum: New York, 1988; pp 227-236.
21. Weinhold, F. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R.; Allinger, N. L.; Clark, T.; Gasteiger, J.; Kollman, P. A.; Schaefer, III, H. F.; Schreiner, P. R., Eds.; John Wiley & Sons: UK, 1998; Vol. 3, pp 1792-1811.
22. Weinhold, F.; Landis, C. R. Chem. Educ. Res. Pract. Eur. 2001, 2, 91-104.
23. Abel, E. W.; Butler, I. S.; Reid, J. G. J. Chem. Soc. 1963, 2068-2070.
24. nd Ed.; Academic Press: New York, 1980.
25. See references 1 ∼ 3 for evaluation of Δσ.
26. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
27. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
28. Hay, P. J.;Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
29. Hay, P. J.;Wadt,W. R. J. Chem. Phys. 1985, 82, 299-310.
30. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654.
31. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639-5648.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.;Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.;Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.;Gomperts, R.;Martin, R. L.; Fox,D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.11; Gaussian, Inc.: Pittsburgh, PA, 1998. Source code has been complied under Mandrake Linux operating systems (release 10.1, kernel 2.6.8.1-24mdksmp).
33. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO, Version 5.0; Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 2001 (http://www.chem.wisc.edu/~nbo5). Source code has been merged to Gaussian 98 to replace the old version of NBO program.
34. 3 can be viewed as a π-accepting ligand, see "Morris, R. J.; Girolami, G. S. Inorg. Chem. 1990, 29, 4167-4169."
35. Bush, R. C.; Angelici, R. J. Inorg. Chem. 1988, 27, 681-686.
36. Natural Population Analysis (NPA) results are based on "Uddin, J.; Boehme, C.; Frenking, G. Organometallics 2000, 19, 571-582."
37. Type "pop=NBODel" in route section of Gaussian98 to use NBO DELETION ($DEL) http://www.chem.wisc.edu/~nbo5/tut-del.htm
38. The term "rehybridization" quoted for changes of %p is borrowed from "Alabugin, I.V.; Manoharan, M.; Peabody, S.; Weinhold, F. J. Am. Chem. Soc. 2003, 125, 5973-5987."
39. Bent, H. A. Chem. Rev. 1961, 61, 275-311.
40. Mehner, T.; Schnöckel, H.; Almond, M. J.; Downs, A. J. J. Chem. Soc., Chem. Commun. 1988, 117-119.