The "hockey sticks" effect revisited: The conformational and electronic properties of 3,7-dithia-1,5-diazabicyclo[3.3.1]nonane from the QTAIM perspective

Journal of Physical Chemistry A

Volumn 115, Issue 45, 2011, Pages 12738-12745

  Bushmarinov, I S ^a   Fedyanin, I V ^a   Lyssenko, K A ^a   Lapteva, V L ^b   Pisarev, S A ^c   Palyulin, V A ^b   Zefirov, N S ^b   Antipin, M Yu ^a  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c INSTITUTE OF PHYSIOLOGICALLY ACTIVE COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC ENERGIES; CONFORMATIONAL EFFECT; INTRA-MOLECULAR BONDING; QUANTUM THEORY OF ATOMS IN MOLECULES; RELATIVE STABILITIES; STEREOELECTRONIC INTERACTIONS; THEORETICAL EXPLANATION; TOPOLOGICAL ANALYSIS;

ELECTRONIC PROPERTIES; QUANTUM THEORY;

CONFORMATIONS;

AZABICYCLO DERIVATIVE;

CHEMISTRY; CONFORMATION; ELECTRON; QUANTUM THEORY; REVIEW;

AZABICYCLO COMPOUNDS; ELECTRONS; MOLECULAR CONFORMATION; QUANTUM THEORY;

EID: 80855129495     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp203730b     Document Type: Review

References (66)

1. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press, New York, 1994.
2. Bader, R. F. W.; Bayles, D. J. Phys. Chem. A 2000, 104, 5579-5589
3. Cortés-Guzmán, F.; Bader, R. F. W. Chem. Phys. Lett. 2003, 379, 183-192
4. Bader, R. F. W. J. Phys. Chem. A 2008, 112, 13717-13728
5. Wiberg, K. B.; Bader, R. F. W.; Lau, C. D. H. J. Am. Chem. Soc. 1987, 109, 1001-1012
6. Koch, U.; Popelier, P. L. A. J. Phys. Chem. 1995, 99, 9747-9754
7. Matta, C. F.; Hernández-Trujillo, J.; Tang, T.-H.; Bader, R. F. W. Chem.-Eur. J. 2003, 9, 1940-1951
8. Popelier, P. L. A. J. Phys. Chem. A 1998, 102, 1873-1878
9. Eskandari, K.; Vila, A.; Mosquera, R. A. J. Phys. Chem. A 2007, 111, 8491-8499
10. Mandado, M.; Mosquera, R. A.; Alsenoy, C. V. Tetrahedron 2006, 62, 4243-4252
11. Vila, A.; Mosquera, R. A. J. Comput. Chem. 2007, 28, 1516-1530
12. Bushmarinov, I. S.; Antipin, M. Yu.; Akhmetova, V. R.; Nadyrgulova, G. R.; Lyssenko, K. A. J. Phys. Chem. A 2008, 112, 5017-5023
13. Berestovitskaya, V. M.; Makarenko, S. V.; Bushmarinov, I. S.; Lyssenko, K. A.; Smirnov, A. S.; Stukan', E. V. Russ. Chem. Bull. 2010, 58, 1023-1033
14. Kirby, A. J. The anomeric effect and related stereoelectronic effects at oxygen; Springer: Berlin, 1983.
15. Bader, R. F. W. J. Phys. Chem. A 1998, 102, 7314-7323
16. Pendás, A. M.; Francisco, E.; Blanco, M. A.; Gatti, C. Chem.-Eur. J. 2007, 13, 9362-9371
17. Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170-173
18. Espinosa, E.; Lecomte, C.; Molins, E. Chem. Phys. Lett. 1999, 300, 745-748
19. Espinosa, E.; Alkorta, I.; Rozas, I.; Elguero, J.; Molins, E. Chem. Phys. Lett. 2001, 336, 457-461
20. Espinosa, E.; Alkorta, I.; Elguero, J.; Molins, E. J. Chem. Phys. 2002, 117, 5529
21. Espinosa, E.; Molins, E. J. Chem. Phys. 2000, 113, 5686
22. Lyssenko, K. A.; Nelyubina, Yu. V.; Kostyanovsky, R. G.; Antipin, M. Yu. ChemPhysChem 2006, 7, 2453-2455
23. Lyssenko, K. A.; Korlyukov, A. A.; Golovanov, D. G.; Ketkov, S. Y.; Antipin, M. Yu. J. Phys. Chem. A 2006, 110, 6545-6551
24. Lyssenko, K. A.; Korlyukov, A. A.; Antipin, M. Yu. Mendeleev Commun. 2005, 15, 90-92
25. Glukhov, I. V.; Lyssenko, K. A.; Korlyukov, A. A.; Antipin, M. Yu. Faraday Discuss. 2007, 135, 203-215
26. Nelyubina, Yu. V.; Glukhov, I. V.; Antipin, M. Yu.; Lyssenko, K. A. Chem. Commun. 2010, 46, 3469
27. Sobczyk, L.; Grabowski, S. J.; Krygowski, T. M. Chem. Rev. 2005, 105, 3513-3560
28. Pidko, E. A.; van Santen, R. A. ChemPhysChem 2006, 7, 1657-1660
29. Pidko, E. A.; Xu, J.; Mojet, B. L.; Lefferts, L.; Subbotina, I. R.; Kazansky, V. B.; van Santen, R. A. J. Phys. Chem. B 2006, 110, 22618-22627
30. Korlyukov, A. A.; Lyssenko, K. A.; Antipin, M. Yu.; Grebneva, E. A.; Albanov, A. I.; Trofimova, O. M.; Zel'bst, E. A.; Voronkov, M. G. J. Organomet. Chem. 2009, 694, 607-615
31. Puntus, L. N.; Lyssenko, K. A.; Antipin, M. Yu.; Bünzli, J.-C. G. Inorg. Chem. 2008, 47, 11095-11107
32. Borissova, A. O.; Korlyukov, A. A.; Antipin, M. Yu.; Lyssenko, K. A. J. Phys. Chem. A 2008, 112, 11519-11522
33. Nelyubina, Yu. V.; Dalinger, I. L.; Lyssenko, K. A. Angew. Chem., Int. Ed. 2011, 50, 2892-2894
34. Gurskii, M. E.; Lyssenko, K. A.; Karionova, A. L.; Belyakov, P. A.; Potapova, T. V.; Antipin, M. Yu.; Bubnov, Yu. N. Russ. Chem. Bull. 2004, 53, 1963-1977
35. Lyssenko, K. A.; Antipin, M. Yu.; Gurskii, M. E.; Bubnov, Yu. N.; Karionova, A. L.; Boese, R. Chem. Phys. Lett. 2004, 384, 40-44
36. Zefirov, N. S.; Palyulin, V. A. In Topics in Stereochemistry; John Wiley & Sons, Inc.: Hoboken, NJ, 1991; Vol. 20, pp 171-230.
37. Choo, J.; Kim, S.; Joo, H.; Kwon, Y. J. Mol. Struct. THEOCHEM 2002, 619, 113-120
38. Zefirov, N. S. Tetrahedron 1977, 33, 3192
39. Gustaffson, R. Int. J. Sulfur Chem., Part A 1971, 1, 233-241
40. Gleiter, R.; Kobayashi, M.; Zefirov, N. S.; Palyulin, V. A. Proc. Natl. Acad. Sci. USSR 1977, 235, 347-350
41. Cadenas-Pliego, G.; Contreras, R.; Flores-Parra, A.; Daran, J. C.; Halut, S. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 84, 9
42. Potekhin, K. A.; Kurkutova, E. N. Proc. Natl. Acad. Sci. USSR 1977, 813
43. Gleiter, R.; Zefirov, N. S.; Palyulin, V. A.; Potekhin, K. A.; Kurkutova, E. N.; Struchkov, Y. T.; Antipin, M. Yu. Zh. Org. Khim. 1978, 14, 1630-1631
44. Allen, F. H.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. In International Tables for Crystallography; Prince, E., Ed.; International Union of Crystallography: Chester, England, 2006; Vol. C, pp 790-811.
45. Cremer, D.; Kraka, E. Croat. Chem. Acta 1984, 57, 1259-1281
46. McCormack, K. L.; Mallinson, P. R.; Webster, B. C.; Yufit, D. S. Faraday Trans. 1996, 92, 1709
47. Bukalov, S. S.; Leites, L. A.; Lyssenko, K. A.; Aysin, R. R.; Korlyukov, A. A.; Zubavichus, J. V.; Chernichenko, K. Y.; Balenkova, E. S.; Nenajdenko, V. G.; Antipin, M. Yu. J. Phys. Chem. A 2008, 112, 10949-10961
48. Scherer, W.; Spiegler, M.; Pedersen, B.; Tafipolsky, M.; Hieringer, W.; Reinhard, B.; Downs, A. J.; McGrady, G. S. Chem. Commun. 2000, 635-636
49. Nelyubina, Yu. V.; Antipin, M. Yu.; Lyssenko, K. A. J. Phys. Chem. A 2007, 111, 1091-1095
50. Mastryukov, V. S.; Popik, M. V.; Dorofeeva, O. V.; Golubinskii, A. V.; Vilkov, L. V.; Belikova, N. A.; Allinger, N. L. J. Am. Chem. Soc. 1981, 103, 1333-1337
51. Wiberg, K. B.; Bader, R. F. W.; Lau, C. D. H. J. Am. Chem. Soc. 1987, 109, 985-1001
52. Poater, J.; Solà, M.; Bickelhaupt, F. M. Chem.-Eur. J. 2006, 12, 2889-2895
53. Sheldrick, G. Acta Crystallogr., Sect. A 2008, 64, 112-122
54. Koritsansky, T. S.; Howard, S. T.; Richter, T.; Macchi, P.; Volkov, A.; Gatti, C.; Mallinson, P. R.; Farrugia, L. J.; Su, Z.; Hansen, N. K. XD-A Computer program package for multipole refinement and Topological Analysis of charge densities from diffraction data, 2003.
55. Hirshfeld, F. L. Theor. Chim. Acta 1977, 44, 129-138
56. Stash, A.; Tsirelson, V. J. Appl. Crystallogr. 2002, 35, 371-373
57. Kirzhnits, D. A. Sov. Phys. JETP 1957, 5, 64
58. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J.; Vreven, T.; Kudin, K. N.; Burant, J. C. Gaussian 03, Revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
59. Keith, T. A. AIMAll (Version 09.02.01, aim.tkgristmill.com), 2009.
60. Dunning, T. H. J. Chem. Phys. 1989, 90, 1007
61. Granovsky, A. Firefly version 7.1.G, http://classic.chem.msu.su/.
62. Granovsky, A. A. J. Chem. Phys. 2011, 134, 214113
63. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J. Comput. Chem. 1993, 14, 1347-1363
64. EMSL Basis Set Exchange https://bse.pnl.gov/bse/portal (accessed Aug 5, 2011).
65. Schuchardt, K. L.; Didier, B. T.; Elsethagen, T.; Sun, L.; Gurumoorthi, V.; Chase, J.; Li, J.; Windus, T. L. J. Chem. Inf. Model. 2007, 47, 1045-1052
66. Wheeler, S. E.; Houk, K. N.; Schleyer, P. v. R.; Allen, W. D. J. Am. Chem. Soc. 2009, 131, 2547-2560