The smallest borazine-fused cyclacenes: Novel N-H conformations in cyclo-BN-anthracene and cyclo-BN-tetracene from Hartree-Fock and density functional calculations

Journal of Molecular Structure: THEOCHEM

Volumn 893, Issue 1-3, 2009, Pages 9-16

  Johnson, Carey J ^a   Zoellner, Robert W ^a  

^a HUMBOLDT STATE UNIVERSITY   (United States)

Author keywords

BN cyclacene; Borazine; Conformer; cyclo BN anthracene; cyclo BN tetracene

Indexed keywords

EID: 56549119012     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2008.09.012     Document Type: Article

References (94)

1. Ege G., and Vogler H. Theor. Chim. Acta 35 (1974) 189
2. Esser B., Rominger F., and Sleiter R. J. Am. Chem. Soc. 130 (2008) 6716
3. Xu H.-L., Li Z.-R., Wang F.-F., Wu D., Harigaya K., and Gu F.L. Chem. Phys. Lett. 454 (2008) 323
4. Jiang D.-e., and Dai S. J. Phys. Chem. C 112 (2008) 5348
5. Chen Z., Jiang D.-e., Ju X., Bettinger H.G., Dai S., von Schleyer P., and Houk K.N. Org. Lett. 9 (2007) 5449
6. Lepetit C., Zou C., and Chauvin R. J. Org. Chem. 71 (2006) 6317
7. Miller G.P., Okano S., and Tomanek D. J. Chem. Phys. 124 (2006) 121102
8. Azizoglu A. Struct. Chem. 14 (2003) 575
9. Türker L. J. Mol. Struct. THEOCHEM 664-665 (2003) 47
10. Türker L. J. Mol. Struct. THEOCHEM 631 (2003) 87
11. Türker L. J. Mol. Struct. THEOCHEM 587 (2002) 19
12. Türker L. J. Mol. Struct. THEOCHEM 574 (2001) 177
13. Türker L. J. Mol. Struct. THEOCHEM 536 (2001) 235
14. Türker L. J. Mol. Struct. THEOCHEM 531 (2000) 333
15. Türker L., and Celebi N. Ind. J. Chem. 39B (2000) 410
16. Türker L. J. Mol. Struct. THEOCHEM 497 (2000) 11
17. Türker L. Turk. J. Chem. 24 (2000) 217
18. Türker L. J. Mol. Struct. THEOCHEM 490 (1999) 55
19. Türker L. J. Mol. Struct. THEOCHEM 454 (1998) 83
20. Türker L. Turk. J. Chem. 22 (1998) 109
21. Türker L. J. Mol. Struct. 407 (1997) 217
22. Türker L. Turk. J. Chem. 21 (1997) 415
23. Türker L., and Erkoç S. Turk. J. Chem. 21 (1997) 167
24. Türker L. Polycyclic Arom. Comp. 8 (1996) 67
25. Türker L. Polycyclic Arom. Comp. 4 (1995) 231
26. Türker L. Polycyclic Arom. Comp. 4 (1994) 191
27. Irle S., Mews A., and Morokuma K. J. Phys. Chem. A 106 (2002) 11973
28. Houk K.N., Lee P.S., and Nendel M. J. Org. Chem. 66 (2001) 5517
29. Martin-Santamaria S., and Rzepa H.S. J. Chem. Soc. Perkin Trans. II (2000) 2378
30. Choi H.S., and Kim K.S. Angew. Chem. Int. Ed. 38 (1999) 2256
31. Brunborg A.S., Brunvoll J., Cyvin B.N., and Cyvin S.J. Asian J. Spectrosc. 1 (1997) 161
32. Gutman I. Polycyclic Arom. Comp. 8 (1996) 251
33. Gutman I., Biedermann P.U., Ivanov-Petrovic V., and Agranat I. Polycyclic Arom. Comp. 8 (1996) 189
34. Aihara J. J. Chem. Soc. Perkin Trans. II (1994) 971
35. Haase M.A., and Zoellner R.W. J. Org. Chem. 57 (1992) 1031
36. A.J. Dikmans, Synthesis of Belt-Shaped Macrocyclic Cyclophanes. Part I. Synthesis of Key Intermediated in the Proposed Synthesis of [7]- and [8]-Cyclacenes. Part II. Synthesis of Key Intermediated in a Proposed Synthesis of a Cyclic Decaphenylene, Dissertation, University of Western Ontario, 1998.
37. Kintzel O., Luger P., Weber M., and Schlüter A.D. Eur. J. Org. Chem. (1998) 99
38. Kintzel O., and Schlüter A.D. Acta Polym. 48 (1997) 212
39. Cory R.M., and McPhail C.L. Tetrahedron Lett. 37 (1996) 1987
40. Cory R.M., McPhail C.L., Dikmans A.J., and Vittal J.J. Tetrahedron Lett. 37 (1996) 1983
41. Cory R.M., McPhail C.L., and Dikmans A.J. Tetrahedron Lett. 34 (1993) 7533
42. F.A. McCormick, I. Approaches to pentaminocyclopentadienyl cations: Potential components for organic ferromagnets. II. Nonplanar polyacene synthesis: towards [12]cyclacene, Dissertation, Columbia University, 1996.
43. Ashton P.R., Girreser U., Giuffrida D., Kohnke F.H., Mathias J.P., Raymo F.M., Slawin A.M.Z., Stoddart J.F., and Williams D.J. J. Am. Chem. Soc. 115 (1993) 5422
44. Ashton P.R., Brown G.R., Isaacs N.S., Giuffrida D., Kohnke F.H., Mathias J.P., Slawin A.M.Z., Smith D.R., Stoddart J.F., and Williams D.J. J. Am. Chem. Soc. 114 (1992) 6330
45. Ashton P.R., Isaacs N.S., Kohnke F.H., Mathias J.P., and Stoddart J.F. Angew. Chem. 101 (1989) 1266
46. Ellwood P., Mathias J.P., Stoddart J.F., and Kohnke F.H. Bull. Soc. Chem. Belg. 97 (1988) 669
47. Ashton P.R., Isaacs N.S., Kohnke F.H., Slawin A.M.Z., Spencer C.M., Stoddart J.F., and Williams D.J. Angew. Chem. 100 (1988) 981
48. Kohnke F.H., Slawin A.M.Z., Stoddart J.F., and Williams D.J. Angew. Chem. 99 (1987) 941
49. Hollis T.K., Rheingold A.L., Robinson N.P., Whelan J., and Bosnich B. Organometallics 11 (1992) 2812
50. Yao T., Yu H., Vermeij R.J., and Bodwell G.J. Pure Appl. Chem. 80 (2008) 533
51. Gleiter R., Hellbach B., Gath S., and Schaller R.J. Pure Appl. Chem. 78 (2006) 699
52. Tahara K., and Tobe Y. Chem. Rev. 106 (2006) 5274
53. Herges R. In: Gleiter R., and Hopf H. (Eds). Modern Cyclophane Chemistry (2004), Wiley-VCH, Weinheim, Germany 337
54. Türker L., and Gümüs S. J. Mol. Struct. THEOCHEM 685 (2004) 1
55. Scott L.T. Angew. Chem. 115 (2003) 4265
56. Cory R.M., and McPhail C.L. Adv. Theor. Interest. Mol. 4 (1998) 53
57. Inazu T., and Takemura H. Kagaku (Kyoto) 51 (1996) 596
58. Schröder A., Mekelburger H.-B., and Vögtle F. Top. Curr. Chem. 172 (1994) 179
59. Kohnke F.H., Mathias J.P., and Stoddart J.F. Top. Curr. Chem. 165 (1993) 1
60. Girreser U., Giuffrida D., Kohnke F.H., Mathias J.P., Philp D., and Stoddart J.F. Pure Appl. Chem. 65 (1993) 119
61. Mathias J.P., and Stoddart J.F. Chem. Soc. Rev. 21 (1992) 215
62. Kohnke F.H., Mathias J.P., and Stoddart J.F. Spec. Publ. R. Soc. Chem. 78 (1989) 243
63. Kohnke F.H., and Stoddart J.F. Pure Appl. Chem. 61 (1989) 1581
64. Stoddart J.F. Chem. Brit. 24 (1988) 1203
65. Türker L., and Gümüs S. J. Mol. Struct. THEOCHEM 679 (2004) 143
66. Türker L., and Celebi N. Bull. Soc. Chim. Belg. 106 (1997) 201
67. Türker L. Polycyclic Arom. Comp. 12 (1997) 139
68. Türker L. Polycyclic Arom. Comp. 12 (1997) 213
69. Türker L. J. Mol. Struct. THEOCHEM 468 (1999) 67
70. Türker L., and Bayer I. J. Phys. Chem. Solids 61 (2000) 1041
71. Türker L. J. Mol. Struct. THEOCHEM 531 (2000) 175
72. Türker L., and Azizoglu A. J. Mol. Struct. THEOCHEM 535 (2001) 151
73. Türker L., and Gümüs S. J. Mol. Struct. THEOCHEM 674 (2004) 185
74. Türker L. J. Mol. Struct. THEOCHEM 492 (1999) 159
75. Türker L., and Erkoç S. J. Mol. Struct. THEOCHEM 636 (2003) 143
76. Erkoç S., and Malcioglu O.B. Int. J. Mod. Phys. C 14 (2003) 1183
77. Türker L. Rare Met. (Beij.) 19 (2000) 53
78. Erkoç S. J. Mol. Struct. THEOCHEM 540 (2001) 153
79. Türker L. J. Mol. Struct. THEOCHEM 640 (2003) 63
80. Yang S.W., Zhang H., Soon J.M., Lin C.W., Wu P., and Loh K.P. Diamond Rel. Mat. 12 (2003) 1194
81. Loh K.P., Yang S.W., Soon J.M., Zhang H., and Wu P. J. Phys. Chem. A 107 (2003) 5555
82. B.J. Deppmeier, A.J. Driessen, W.J. Hehre, J.A. Johnson, P.E. Klunzinger, M. Watanabe, PC Spartan Pro version 1.0.8, Wavefunction, Inc., Irvine, CA, 2001.
83. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morojuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacomb, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98W, Gaussian, Inc., Pittsburgh, PA, 1998.
84. Ditchfield R., Hehre W.J., and Pople J.A. J. Chem. Phys. 54 (1971) 724
85. Heher W.J., Ditchfield R., and Pople J.A. J. Chem. Phys. 56 (1972) 2257
86. Hariharan P.C., and Pople J.A. Mol. Phys. 27 (1974) 209
87. Gordon M.S. Chem. Phys. Lett. 76 (1980) 163
88. Hariharan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213
89. Binning Jr. R.C., and Curtiss L.A. J. Comp. Chem. 11 (1990) 1206
90. Becke A.D. J. Chem. Phys. 98 (1993) 5648
91. Tonmunphean S., Wijitkosoom A., Tantirungrotechai Y., Nuttavut N., and Limtrakul J. Bull. Chem. Soc. Japan 76 (2003) 1537
92. Greenwood N.N., and Earnshaw A. Chemistry of the Elements. Second ed. (1997), Butterworth-Heinemann, Oxford, UK
93. Corfield P.W.R., and Shore S.G. J. Am. Chem. Soc. 95 (1973) 1480
94. Hunter G., Wadsworth Jr. W.S., and Mislow K. Organometallics 1 (1982) 968