An 17O NMR and quantum chemical study of monoclinic and orthorhombic polymorphs of triphenylphosphine oxide

Inorganic Chemistry

Volumn 42, Issue 17, 2003, Pages 5085-5096

  Bryce, David L ^a   Eichele, Klaus ^b   Wasylishen, Roderick E ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

OXYGEN 17; PHOSPHINE OXIDE DERIVATIVE; TRIPHENYLPHOSPHINE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL SHIFT TENSOR; DIPOLE; ELECTRIC FIELD; ELECTRIC FIELD GRADIENT; GEOMETRY; MAGIC ANGLE SPINNING NUCLEAR MAGNETIC RESONANCE; MATERIALS; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGEN NUCLEAR MAGNETIC RESONANCE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; SOLID; THEORY;

EID: 0043011170     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic020706p     Document Type: Article

References (150)

1. Pomerantz, M.; Terrazas, M. S.; Cheng, Y.; Gu, X. Phosphorus, Sulfur Silicon 1996, 109-110, 505-508.
2. Grossmann, G.; Gruner, M.; Seifert, G. Z. Chem. 1976, 16, 362-363.
3. Gray, G. A.; Albright, T. A. J. Am. Chem. Soc. 1977, 99, 3243-3250.
4. Dahn, H.; Toan, V. V.; Ung-Truong, M.-N. Magn. Reson. Chem. 1992, 30, 1089-1096.
5. Christ, H. A.; Diehl, P. Helv. Phys. Acta 1963, 36, 170-182.
6. Christ, H. A.; Diehl, P.; Schneider, HR.; Dahn, H. Helv. Chim. Acta 1961, 44, 865-880.
7. Quin, L. D.; Szewczyk, J.; Linehan, K.; Harris, D. L. Magn. Reson. Chem. 1987, 25, 271-273.
8. Szewczyk, J.; Linehan, K.; Quin, L. D. Phosphorus Sulfur 1988, 37, 35-40.
9. McFarlane, H. C. E.; McFarlane, W. J. Chem. Soc., Chem. Commun. 1978, 531-532.
10. Hibbert, R. C.; Logan, N. J. Chem. Soc., Dalton Trans. 1985, 865-866.
11. 17O NMR Spectroscopy in Organic Chemistry: Boykin, D. W., Ed.; CRC Press: Boca Raton, FL, 1991: Chapter 10.
12. Davies, J. A.; Dutremez, S.; Pinkerton, A. A. Inorg. Chem. 1991, 30, 2380-2387.
13. Calcagno, P.; Kariuki, B. M.; Kitchin, S. J.; Robinson, J. M. A.; Philp, D.; Harris, K. D. M. Chem. Eur. J. 2000, 6, 2338-2349.
14. Arumugam, S.; Glidewell, C.; Harris, K. D. M. J. Chem. Soc., Chem. Commun. 1992, 724-726.
15. Lynch, D. E.; Smith, G.; Byriel, K. A.; Kennard, C. H. L.; Kwiatkowski, J.; Whittaker, A. K. Aust. J. Chem. 1997, 50, 1191-1194.
16. Lagier, C. M.; Scheler, U.; McGeorge, G.; Sierra, M. G.; Olivieri, A. C. ; Harris, R. K. J. Chem. Soc., Perkin Trans 2 1996, 1325-1329.
17. Apperley, D. C.; Chaloner, P. A.; Crowe, L. A.; Harris, R. K.; Harrison, R. M.; Hitchcock, P. B.; Lagier, C. M. Phys. Chem. Chem. Phys. 2000, 2, 3511-3518.
18. Hargé, J.-C.; El Abdallaoui, H. E. A.; Rubini, P. Magn. Reson. Chem. 1993, 31, 752-757.
19. Rubini, P.; El Alaoui El Abdallaoui, H. Phosphorus, Sulfur Silicon 1994, 97, 57-61.
20. Lagier, C. M.; Olivieri, A. C.; Harris, R. K. J. Chem. Soc., Perkin Trans. 2 1998, 1791-1796.
21. Dutasta, J. P.; Robert, J. B.; Wiesenfeld, L. In Phosphorus Chemistry: Proceedings of the 1981 International Conference; Quin, L. D., Verkade, J. G., Eds.; ACS Symposium Series 171; American Chemical Society: Washington, DC, 1981; pp 581-584.
22. Bemi, L.; Clark, H. C.; Davies, J. A.; Fyfe, C. A.; Wasylishen, R. E. J. Am. Chem. Soc. 1982, 104, 438-445.
23. El Alaoui El Abdallaoui, H.; Rubini, P. Spectrochim. Acta A 1993, 49, 329-338.
24. Montana, A. J.; Zumbulyadis, N.; Dailey, B. P. J. Am. Chem. Soc. 1977, 99, 4290-4293.
25. Robert, J. B.; Wiesenfeld, L. Mol. Phys. 1981, 44, 319-327.
26. Berger, S.; Braun, S.; Kalinowski, H.-O. NMR Spectroscopy of the Non-Metallic Elements; Becconsall, J., English language translation; John Wiley & Sons: Chichester, U.K., 1997; Chapter 5.
27. (a) Gerothanassis, I. P.; Momenteau, M. J. Am. Chem. Soc. 1987, 109, 6944-6947.
28. (b) Gerothanassis, I. P.; Momenteau, M.; Loock, B. J. Am. Chem. Soc. 1989, 111, 7006-7012.
29. McFarlane, W.; McFarlane, H. C. E. In Multinuclear NMR; Mason, J., Ed.; Plenum: New York, 1987; Chapter 14.
30. Gerothanassis, I. P. In Encyclopedia of Nuclear Magnetic Resonance; Grant, D. M., Harris, R. K., Eds.; Wiley Inc.: Chichester, U.K., 1996; pp 3430-3440.
31. Kintzinger, J. P. In NMR of Newly Accessible Nuclei; Laszlo, P., Ed.; Academic Press: New York, 1983; Chapter 4.
32. 17O NMR Spectroscopy in Organic Chemistry; Boykin, D. W., Ed.; CRC Press: Boca Raton, FL, 1991; Chapter 1.
33. Gilheany, D. G. In The Chemistry of Organophosphorus Compounds, Volume 2: Phosphine Oxides, Sulphides, Selenides and Tellurides; Hartley, F. R., Ed.; John Wiley and Sons: Chichester, U.K., 1992; Chapter 1.
34. Burford, N. Coord. Chem. Rev. 1992, 112, 1-18.
35. Schmidt, M. W.; Gordon, M. S. J. Am. Chem. Soc. 1985, 107, 1922-1930.
36. Rai, U. S.; Symons, M. C. R. J. Chem. Soc., Faraday Trans. 1994, 90, 2649-2652.
37. Chesnut, D. B. J. Am. Chem. Soc. 1998, 120, 10504-10510.
38. Gilheany, D. G. Chem. Rev. 1994, 94, 1339-1374.
39. See, R. F.; Dutoi, A. D.; Fettinger, J. C.; Nicastro, P. J.; Ziller, J. W. J. Chem. Crystallogr. 1998, 28, 893-898.
40. Sandblom, N.; Ziegler, T.; Chivers, T. Can. J. Chem. 1996, 74, 2363-2371.
41. Cooper, D. L.; Cunningham, T. P.; Gerratt, J.; Karadakov, P. B.; Raimondi, M. J. Am. Chem. Soc. 1994, 116, 4414-4426.
42. Dobado, J. A.; Martínez-García, H.; Molina, J. M.; Sundberg, M. R. J. Am. Chem. Soc. 1998, 120, 8461-8471.
43. Brock, C. P.; Schweizer, W. B.; Dunitz, J. D. J. Am. Chem. Soc. 1985, 107, 6964-6970.
44. Thomas, J. A.; Hamor, T. A. Acta Crystallogr. 1993, C49, 355-357.
45. Spek, A. L. Acta Crystallogr. 1987, C43, 1233-1235.
46. Baures, P. W.; Silverton, J. V. Acta Crystallogr. 1990, C46, 715-717.
47. Ruban, G.; Zabel, V. Cryst. Struct. Commun. 1976, 5, 671-677.
48. Gusev, A. I.; Bokii, N. G.; Afonina, N. N.; Timofeeva, T. V.; Kalinin, A. E.; Struchkov, Yu. T. J. Struct. Chem. (Engl.Transl.) 1973, 14, 101-108;
49. Zh. Strukt. Khim. 1973, 14, 115-125.
50. Bandoli, G.; Bortolozzo, G.; Clemente, D. A.; Croatto, U.; Panattoni, C. J. Chem. Soc. A 1970, 2778-2780.
51. Etter, M. C.; Baures, P. W. J. Am. Chem. Soc. 1988, 110, 639-640.
52. (a) Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3440-3461.
53. (c) Dunitz, J. D.; Bernstein, J. Acc. Chem. Res. 1995, 28, 193-200.
54. Desiraju, G. R. Nat. Mater. 2002, 1, 77-79.
55. Desiraju, G. R. Science 1997, 278, 404-405.
56. Harris, R. K. In Encyclopedia of Nuclear Magnetic Resonance; Grant, D. M., Harris, R. K., Eds.; Wiley Inc.: Chichester, U.K., 1996; pp 3734-3740.
57. Padden, B. E.; Zell, M. T.; Dong, Z.; Schroeder, S. A.; Grant, D. J. W.; Munson, E. J. Anal. Chem. 1999, 71, 3325-3331.
58. Liang, J.; Ma, Y.; Chen, B.; Munson, E. J.; Davis, H. T.; Binder, D.; Chang, H.-T.; Abbas, S.; Hsu, F.-L. J. Phys. Chem. B 2001, 105, 9653-9662.
59. Sidhu, P. S.; Enright, G. D.; Ripmeester, J. A.; Penner, G. H. J. Phys. Chem. B 2002, 106, 8569-8581.
60. Harper, J. K.; Facelli, J. C.; Barich, D. H.; McGeorge, G.; Mulgrew, A. E.; Grant, D. M. J. Am. Chem. Soc. 2002, 124, 10589-10595.
61. Medek, A.; Frydman, L. J. Am. Chem. Soc. 2000, 122, 684-691.
62. Middleton, D. A.; Le Duff, C. S.; Peng, X.; Reid, D. G.; Saunders, D. J. Am. Chem. Soc. 2000, 122, 1161-1170.
63. Apperley, D. C.; Fletton, R. A.; Harris, R. K.; Lancaster, R. W.; Tavener, S.; Threlfall, T. L. J. Pharm. Sci. 1999, 88, 1275-1280.
64. Mason, J. Solid State Nucl. Magn. Reson. 1993, 2, 285-288.
65. Mills, I.; Cvitaš, T.; Homann, K.; Kallay, N.; Kuchitsu, K. Quantities, Units and Symbols in Physical Chemistry, 2nd ed.; Blackwell Science: Oxford, U.K., 1993.
66. Eichele, K.; Wasylishen, R. E.; Nelson, J. H. J. Phys. Chem. A 1997, 101, 5463-5468.
67. (a) VanderHart, D. L.; Gutowsky, H. S.; Farrar, T. C. J. Chem. Phys. 1969, 50, 1058-1065.
68. (b) Harris, R. K.; Packer, K. J.; Thayer, A. M. J. Magn. Reson. 1985, 62, 284-297.
69. (c) Grimmer, A.-R.; Neels, J. Z. Anorg. Allg. Chem. 1989, 576, 117-130.
70. Wasylishen, R. E. In Encyclopedia of Nuclear Magnetic Resonance; Grant, D. M., Harris, R. K., Eds.; Wiley Inc.: Chichester, U.K., 1996; pp 1685-1695.
71. Hays, H. R.; Peterson, D. J. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley-Interscience: New York, 1972; Vol. 3, Chapter 6.
72. Bennett, A. E.; Rienstra, C. M.; Auger, M.; Lakshmi, K. V.; Griffin, R. G. J. Chem. Phys. 1995, 103, 6951-6958.
73. Eichele, K.; Wasylishen, R. E. WSOLIDS NMR Simulation Package, version 1.17.26: 2000.
74. Alderman, D. W.; Solum, M. S.; Grant, D. M. J. Chem. Phys. 1986, 84, 3717-3725.
75. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, 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.; 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.; Gonzalez C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7: Gaussian, Inc.: Pittsburgh, PA, 1998.
76. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
77. (a) Ditchfield, R. Mol. Phys. 1974, 27, 789-807.
78. (b) Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.
79. (a) Chesnut, D. B.; Moore, K. D. J. Comput. Chem. 1989, 10, 648-659.
80. (b) Chesnut, D. B.; Rusiloski, B. E.; Moore, K. D.; Egolf, D. A. J. Comput. Chem. 1993, 14, 1364-1375.
81. Wasylishen, R. E.; Bryce, D. L. J. Chem. Phys. 2002, 117, 10061-10066.
82. Sundholm, D.; Olsen, J. J. Phys. Chem. 1992, 96, 627-630.
83. (a) Pyykkö, P. Mol. Phys. 2001, 19, 1617-1629.
84. (b) Pyykkö, P. Z. Naturforsch. 1992, 47a, 189-196.
85. Helgaker, T.; Jensen, H. J. Aa.; Jørgensen, P.; Olsen, P. J.; Ruud, K.; Agren, H.; Andersen, H. T.; Bak, K. L.; Bakken, V.; Christiansen, O.; Dahle, P.; Dalskov, E. K.; Enevoldsen, T.; Fernandez, B.; Heiberg, H.; Hettema, H.; Jonsson, D.; Kirpekar, S.; Kobayashi, R.; Koch, H.; Mikkelsen, K. V.; Norman, P.; Packer, M. J.; Saue, T.; Taylor, P. R.; Vahtras, O. Dalton: An electronic structure program, release 1.0; 1997.
86. (a) Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007-1023.
87. (b) Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1995, 103, 4572-4585.
88. (c) Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 98, 1358-1371.
89. Stewart, E. L.; Nevins, N.; Allinger, N. L.; Bowen, J. P. J. Org. Chem. 1997, 62, 5198-5207.
90. (a) Autschbach, J.; Ziegler, T. J. Chem. Phys. 2000, 113, 936-947.
91. (b) Autschbach, J.; Ziegler, T. J. Chem. Phys. 2000, 113, 9410-9418.
92. (a) Dickson, R. M.; Ziegler, T. J. Phys. Chem. 1996, 100, 5286-5290.
93. (b) Khandogin, J.; Ziegler, T. Spectrochim. Acta, Part A 1999, 55, 607-624.
94. (a) ADF, version 2000.01; Theoretical Chemistry, Vrije Universiteit: Amsterdam; http://www.scm.com.
95. (b) Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41-51.
96. (c) Versluis, L.; Ziegler, T. J. Chem. Phys. 1988. 88, 322-328.
97. (d) te Velde, G.; Baerends, E. J. J. Comput. Phys. 1992, 99, 84-98.
98. (e) Fonseca Guerra, C.; Snijders, J. G.; te Velde, G.; Baerends, E. J. Theor. Chem. Acc. 1998, 99, 391-403.
99. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211.
100. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
101. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824; 1986, 34, 7406.
102. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824; 1986, 34, 7406.
103. Brown, T. L.; Cheng, C. P. Faraday Symp. Chem. Soc. 1978, 13, 75-82.
104. Cheng, C. P.; Brown, T. L. J. Am. Chem. Soc. 1980, 102, 6418-6421.
105. Lucken, E. A. C. In Advances in Nuclear Quadrupole Resonance; Smith, J. A. S., Ed.; John Wiley & Sons: Chichester, U.K., 1983; Vol. 5, Chapter 3.
106. Dunitz, J. D.; Maverick, E. F.; Trueblood, K. N. Angew. Chem., Int. Ed. 1988, 27, 880-895.
107. Cohen, E. A.; Pickett, H. M. J. Mol. Struct. 1983, 97, 97-100.
108. Kaupp, M.; Rovira, C.; Parrinello, M. J. Phys. Chem. B 2000, 104, 5200-5208.
109. Wu, G.; Dong, S.; Ida, R. Chem. Commun. 2001, 891-892.
110. Scheubel, W.; Zimmerman, H.; Haeberlen, U. J. Magn. Reson. 1985, 63, 544-555.
111. Hexem, J. G.; Frey, M. H.; Opella, S. J. J. Chem. Phys. 1982, 77, 3847-3856.
112. Olivieri, A. C.; Frydman, L.; Diaz, L. E. J. Magn. Reson. 1987, 75, 50-62.
113. Olivieri, A.; Frydman, L.; Grasselli, M.; Diaz, L. Magn. Reson. Chem. 1988, 26, 615-618.
114. Olivieri, A. C. J. Magn. Reson. 1989, 81, 201-205.
115. (a) Grasselli, M.; Diaz, L. E.; Olivieri, A. C. Spectrosc. Lett. 1991, 24, 895-907.
116. (b) Eichele, K.; Wasylishen, R. E. Solid State Nucl. Magn. Reson. 1992, 1, 159-163.
117. (c) Gan, Z.; Grant, D. M. J. Magn. Reson. 1990, 90, 522-534.
118. Harris, R. K.; Olivieri, A. C. Prog. NMR Spectrosc. 1992, 24, 435-456.
119. Eichele, K.; Wasylishen, R. E. Inorg. Chem. 1994, 33, 2766-2773.
120. Harris, R. K. Nuclear Magnetic Resonance Spectroscopy: A Physicochemical View; Longman: Malaysia, 1986; Section 5-12.
121. Gerlt, J. A.; Demou, P. C.; Mehdi, S. J. Am. Chem. Soc. 1982, 104, 2848-2856.
122. Sammons, R. D.; Frey, P. A.; Bruzik, K.; Tsai, M.-D. J. Am. Chem. Soc. 1983, 105, 5455-5461.
123. Eichele, K.; Wasylishen, R. E.; Schurko, R. W.; Burford, N.; Whitla, W. A. Can. J. Chem. 1996, 74, 2372-2377.
124. Karaghiosoff, K. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; G. Thieme Verlag: Stuttgart, Germany, 1990; pp 463-471.
125. Gorenstein, D. G. In Phosphorus-31 NMR: Principles and Applications; Gorenstein, D. G., Ed.; Academic Press: New York, 1984; Chapter 2.
126. Alei, M., Jr. J. Chem. Phys. 1965, 43, 2904-2906.
127. Wu, G.; Yamada, K.; Dong, S.; Grondey, H. J. Am. Chem. Soc. 2000, 122, 4215-4216.
128. Yamada, K.; Dong, S.; Wu, G. J. Am. Chem. Soc. 2000, 122, 11602-11609.
129. Power, W. P. J. Am. Chem. Soc. 1995, 117, 1800-1806.
130. Ramsey, N. F. Molecular Beams; Oxford University Press: London. 1956: pp 162-166, 208-213.
131. (a) Ramsey, N. F. Phys. Rev. 1950, 77, 567.
132. (b) Ramsey, N. F. Phys. Rev. 1950, 78, 699-703.
133. (c) Ramsey, N. F. Phys. Rev. 1951, 83, 540-541.
134. (d) Ramsey, N. F. Phys. Rev. 1952, 86, 243-246.
135. Schindler, M.; Kutzelnigg, W.; J. Chem. Phys. 1982, 76, 1919-1933.
136. Cornet, R.; Landsberg, B. M.; Winnewisser, G. J. Mol. Spectrosc. 1980, 82, 253-263.
137. Jameson, C. J. In Specialist Periodical Reports; Webb, G. A., Ed.; Royal Society of Chemistry: London, 1989; Vol. 18, Chapter 1.
138. Malli, G.; Froese, C. Int. J. Quantum Chem. 1967, 1S, 95-98.
139. Cameron, T. S. Unpublished results.
140. Ishii, Y.; Terao, T.; Hayashi, S. J. Chem. Phys. 1997, 107, 2760-2774.
141. Carravetta, M.; Eden, M.; Johannessen, O. G.; Luthman, H.; Verdegem, P. J. E.; Lugtenburg, J.; Sebald, A.; Levitt, M. H. J. Am. Chem. Soc. 2001, 123, 10628-10638.
142. Ishii, Y. J. Chem. Phys. 2001, 114, 8473-8483.
143. Case, D. A. J. Biomol. NMR 1999, 15, 95-102.
144. Eggenberger, R.; Gerber, S.; Huber, H.; Searles, D.; Welker, M. J. Mol. Spectrosc. 1992, 151, 474-481.
145. (a) Ludwig, R.; Weinhold, F.; Farrar, T. C. J. Chem. Phys. 1995, 103, 6941-6950.
146. (b) Ludwig, R.; Weinhold, F.; Farrar, T. C. J. Chem. Phys. 1996, 105, 8223-8230.
147. De Luca, G.; Russo, N.; Köster, A. M.; Calaminici, P.; Jug, K. Mol. Phys. 1999, 97, 347-354.
148. Ahmad, I. K.; Ozeki, H.; Saito, S. J. Chem. Phys. 1999, 110, 912-917.
149. Cazzoli, G.; Dore, L.; Puzzarini, C.; Beninati, S. Phys. Chem. Chem. Phys. 2002, 4, 3575-3577.
150. Armstrong, R. S.; Aroney, M. J.; Le Fèvre, R. J. W.; Pierens, R. K.; Saxby, J. D.; Wilkins, C. J. J. Chem. Soc. A 1969, 2735-2739.