Empirical relationship between the conformation and the direction of carbonyl group pyramidalization of cyclohexanones

Journal of Organic Chemistry

Volumn 64, Issue 22, 1999, Pages 8177-8182

  Laube, Thomas ^a,b  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b Cilag AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; CYCLOHEXANONE DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CONFORMATION; CORRELATION FUNCTION; CRYSTAL STRUCTURE;

EID: 0033615592     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990661i     Document Type: Article

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41. Precise gas-phase structures of simple ketones have been determined by various methods. Cyclopentanone: Kim, H.; Gwinn, W. D. J. Chem. Phys. 1969, 51, 1815-1819. Cyclohexanone: Alonso, J. L. J. Mol. Struct. 1981, 73, 63-69. Dillen, J.; Geise, H. J. J. Mol. Struct. 1980, 69, 137-144. Cycloheptanone: Dillen, J.; Geise, H. J. J. Mol. Struct. 1981, 72, 247-255. 3-Pentanone: Crowder, G. A., Lin, Q. Vib. Spectrosc. 1997, 14, 287-297. Kuze, N.; Kojima, E.; Fujiwara, H.; Takeuchi, H.; Egawa, T.; Konaka, S. J. Mol. Struct. 1996, 375, 231-241. In all of these cases, carbonyl planarity is assumed. For carbonyl pyramidalization in electronically excited states see, e.g.: van der Burgt, M. J.; Huizer, A. H.; Varma, C. A. G. O.; Wagner, B. D.; Lusztyk, J. Chem. Phys. 1995, 196, 193-210. Laane, J.; Zhang, J.; Chiang, W.-Y.; Sagear, P.; Cheatham, C. M. In Structure and Dynamics of Non-Rigid Molecular Systems; Smeyers, Y. G., Ed.; Kluwer: Dordrecht, 1995; pp 181-201.
42. Precise gas-phase structures of simple ketones have been determined by various methods. Cyclopentanone: Kim, H.; Gwinn, W. D. J. Chem. Phys. 1969, 51, 1815-1819. Cyclohexanone: Alonso, J. L. J. Mol. Struct. 1981, 73, 63-69. Dillen, J.; Geise, H. J. J. Mol. Struct. 1980, 69, 137-144. Cycloheptanone: Dillen, J.; Geise, H. J. J. Mol. Struct. 1981, 72, 247-255. 3-Pentanone: Crowder, G. A., Lin, Q. Vib. Spectrosc. 1997, 14, 287-297. Kuze, N.; Kojima, E.; Fujiwara, H.; Takeuchi, H.; Egawa, T.; Konaka, S. J. Mol. Struct. 1996, 375, 231-241. In all of these cases, carbonyl planarity is assumed. For carbonyl pyramidalization in electronically excited states see, e.g.: van der Burgt, M. J.; Huizer, A. H.; Varma, C. A. G. O.; Wagner, B. D.; Lusztyk, J. Chem. Phys. 1995, 196, 193-210. Laane, J.; Zhang, J.; Chiang, W.-Y.; Sagear, P.; Cheatham, C. M. In Structure and Dynamics of Non-Rigid Molecular Systems; Smeyers, Y. G., Ed.; Kluwer: Dordrecht, 1995; pp 181-201.
43. Precise gas-phase structures of simple ketones have been determined by various methods. Cyclopentanone: Kim, H.; Gwinn, W. D. J. Chem. Phys. 1969, 51, 1815-1819. Cyclohexanone: Alonso, J. L. J. Mol. Struct. 1981, 73, 63-69. Dillen, J.; Geise, H. J. J. Mol. Struct. 1980, 69, 137-144. Cycloheptanone: Dillen, J.; Geise, H. J. J. Mol. Struct. 1981, 72, 247-255. 3-Pentanone: Crowder, G. A., Lin, Q. Vib. Spectrosc. 1997, 14, 287-297. Kuze, N.; Kojima, E.; Fujiwara, H.; Takeuchi, H.; Egawa, T.; Konaka, S. J. Mol. Struct. 1996, 375, 231-241. In all of these cases, carbonyl planarity is assumed. For carbonyl pyramidalization in electronically excited states see, e.g.: van der Burgt, M. J.; Huizer, A. H.; Varma, C. A. G. O.; Wagner, B. D.; Lusztyk, J. Chem. Phys. 1995, 196, 193-210. Laane, J.; Zhang, J.; Chiang, W.-Y.; Sagear, P.; Cheatham, C. M. In Structure and Dynamics of Non-Rigid Molecular Systems; Smeyers, Y. G., Ed.; Kluwer: Dordrecht, 1995; pp 181-201.
44. Precise gas-phase structures of simple ketones have been determined by various methods. Cyclopentanone: Kim, H.; Gwinn, W. D. J. Chem. Phys. 1969, 51, 1815-1819. Cyclohexanone: Alonso, J. L. J. Mol. Struct. 1981, 73, 63-69. Dillen, J.; Geise, H. J. J. Mol. Struct. 1980, 69, 137-144. Cycloheptanone: Dillen, J.; Geise, H. J. J. Mol. Struct. 1981, 72, 247-255. 3-Pentanone: Crowder, G. A., Lin, Q. Vib. Spectrosc. 1997, 14, 287-297. Kuze, N.; Kojima, E.; Fujiwara, H.; Takeuchi, H.; Egawa, T.; Konaka, S. J. Mol. Struct. 1996, 375, 231-241. In all of these cases, carbonyl planarity is assumed. For carbonyl pyramidalization in electronically excited states see, e.g.: van der Burgt, M. J.; Huizer, A. H.; Varma, C. A. G. O.; Wagner, B. D.; Lusztyk, J. Chem. Phys. 1995, 196, 193-210. Laane, J.; Zhang, J.; Chiang, W.-Y.; Sagear, P.; Cheatham, C. M. In Structure and Dynamics of Non-Rigid Molecular Systems; Smeyers, Y. G., Ed.; Kluwer: Dordrecht, 1995; pp 181-201.
45. Precise gas-phase structures of simple ketones have been determined by various methods. Cyclopentanone: Kim, H.; Gwinn, W. D. J. Chem. Phys. 1969, 51, 1815-1819. Cyclohexanone: Alonso, J. L. J. Mol. Struct. 1981, 73, 63-69. Dillen, J.; Geise, H. J. J. Mol. Struct. 1980, 69, 137-144. Cycloheptanone: Dillen, J.; Geise, H. J. J. Mol. Struct. 1981, 72, 247-255. 3-Pentanone: Crowder, G. A., Lin, Q. Vib. Spectrosc. 1997, 14, 287-297. Kuze, N.; Kojima, E.; Fujiwara, H.; Takeuchi, H.; Egawa, T.; Konaka, S. J. Mol. Struct. 1996, 375, 231-241. In all of these cases, carbonyl planarity is assumed. For carbonyl pyramidalization in electronically excited states see, e.g.: van der Burgt, M. J.; Huizer, A. H.; Varma, C. A. G. O.; Wagner, B. D.; Lusztyk, J. Chem. Phys. 1995, 196, 193-210. Laane, J.; Zhang, J.; Chiang, W.-Y.; Sagear, P.; Cheatham, C. M. In Structure and Dynamics of Non-Rigid Molecular Systems; Smeyers, Y. G., Ed.; Kluwer: Dordrecht, 1995; pp 181-201.
46. Precise gas-phase structures of simple ketones have been determined by various methods. Cyclopentanone: Kim, H.; Gwinn, W. D. J. Chem. Phys. 1969, 51, 1815-1819. Cyclohexanone: Alonso, J. L. J. Mol. Struct. 1981, 73, 63-69. Dillen, J.; Geise, H. J. J. Mol. Struct. 1980, 69, 137-144. Cycloheptanone: Dillen, J.; Geise, H. J. J. Mol. Struct. 1981, 72, 247-255. 3-Pentanone: Crowder, G. A., Lin, Q. Vib. Spectrosc. 1997, 14, 287-297. Kuze, N.; Kojima, E.; Fujiwara, H.; Takeuchi, H.; Egawa, T.; Konaka, S. J. Mol. Struct. 1996, 375, 231-241. In all of these cases, carbonyl planarity is assumed. For carbonyl pyramidalization in electronically excited states see, e.g.: van der Burgt, M. J.; Huizer, A. H.; Varma, C. A. G. O.; Wagner, B. D.; Lusztyk, J. Chem. Phys. 1995, 196, 193-210. Laane, J.; Zhang, J.; Chiang, W.-Y.; Sagear, P.; Cheatham, C. M. In Structure and Dynamics of Non-Rigid Molecular Systems; Smeyers, Y. G., Ed.; Kluwer: Dordrecht, 1995; pp 181-201.
47. Precise gas-phase structures of simple ketones have been determined by various methods. Cyclopentanone: Kim, H.; Gwinn, W. D. J. Chem. Phys. 1969, 51, 1815-1819. Cyclohexanone: Alonso, J. L. J. Mol. Struct. 1981, 73, 63-69. Dillen, J.; Geise, H. J. J. Mol. Struct. 1980, 69, 137-144. Cycloheptanone: Dillen, J.; Geise, H. J. J. Mol. Struct. 1981, 72, 247-255. 3-Pentanone: Crowder, G. A., Lin, Q. Vib. Spectrosc. 1997, 14, 287-297. Kuze, N.; Kojima, E.; Fujiwara, H.; Takeuchi, H.; Egawa, T.; Konaka, S. J. Mol. Struct. 1996, 375, 231-241. In all of these cases, carbonyl planarity is assumed. For carbonyl pyramidalization in electronically excited states see, e.g.: van der Burgt, M. J.; Huizer, A. H.; Varma, C. A. G. O.; Wagner, B. D.; Lusztyk, J. Chem. Phys. 1995, 196, 193-210. Laane, J.; Zhang, J.; Chiang, W.-Y.; Sagear, P.; Cheatham, C. M. In Structure and Dynamics of Non-Rigid Molecular Systems; Smeyers, Y. G., Ed.; Kluwer: Dordrecht, 1995; pp 181-201.
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