On the aromatic character of 1,2-Dihydro-1,2-azaborine according to magnetic criteria

Journal of Physical Chemistry Letters

Volumn 1, Issue 10, 2010, Pages 1563-1568

  Carion, Raphaël ^a   Liégeois, Vincent ^a   Champagne, Benoît ^a   Bonifazi, Davide ^a   Pelloni, Stefano ^b   Lazzeretti, Paolo ^b  

^a UNIVERSITY OF NAMUR   (Belgium)

^b UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATICITIES; BORAZINE; ELECTRON RESPONSE; MAGNETIC BEHAVIOR; MAGNETIC PERTURBATION; SINGLE-VALUE; VISUALIZATION TOOLS;

BENZENE; HYDROCARBONS; MAGNETIC PROPERTIES; MAGNETISM; VISUALIZATION;

MAGNETIC MATERIALS;

EID: 77952754393     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz100401y     Document Type: Article

References (36)

1. Bosdet, M.; Piers, W. B-N as a C-C Substitute in Aromatic Systems Can. J. Chem. 2009, 87, 8-29
2. Zhang, Z.; Guo, W.; Dai, Y. Stability and Electronic Properties of Small Boron Nitride Nanotubes J. Appl. Phys. 2009, 105, 084312
3. Azadi, S.; Moradian, R. First Principle Study of Unzipped Boron Nitride Nanotubes Phys. Lett. A 2010, 374 (4) 605-609
4. Lee, C. H.; Xie, M.; Kayastha, V.; Wang, J.; Yap, Y. K. Patterned Growth of Boron Nitride Nanotubes by Catalytic Chemical Vapor Deposition Chem. Mater. 2010, 22, 1782-1787
5. Stock, A.; Pohland, E. Boron Hydride. VIII, B2H5 and B5H11 Ber. Dtsch. Chem. Ges. 1926, 59, 2210-2215
6. Massey, S.; Zoellner, R. MNDO Calculations on Borazine Derivatives. The Substitution of One [HNBH] Fragment for One [HCCH] Fragment in Benzene to Form the Azaborines and the Nature of the Cyclotrimer of the 1,2-Isomer Int. J. Quantum Chem. 1991, 39, 789-804
7. Kranz, M.; Clark, T. Azaborines: An Ab Initio Study J. Org. Chem. 1992, 57, 5492-5500
8. Kiran, B.; Phukan, A.; Jemmis, E. Is Borazine Aromatic? Unusual Parallel Behavior Between Hydrocarbons and Corresponding B-N Analogues Inorg. Chem. 2001, 40, 3615-3618
9. Soncini, A.; Domene, C.; Engelberts, J.; Fowler, P.; Rassat, A.; van Lenthe, J.; Havenith, R.; Jenneskens, L. A Unified Orbital Model of Delocalised and Localised Currents in Monocycles, from Annulenes to Azabora-heterocycles Chem.-Eur. J. 2005, 11, 1257-1266
10. Islas, R.; Chamorro, E.; Robles, J.; Heine, T.; Santos, J.; Merino, G. Borazine: To Be or Not to Be Aromatic Struct. Chem. 2007, 18, 833-839
11. Abbey, E.; Zakharov, L.; Liu, S.-Y. Crystal Clear Structural Evidence for Electron Delocalization in 1,2-Dihydro-1,2-azaborines J. Am. Chem. Soc. 2008, 130, 7250-7252
12. Marwitz, A.; Matus, M.; Zakharov, L.; Dixon, D.; Liu, S.-Y. A Hybrid Organic/Inorganic Benzene Angew. Chem., Int. Ed. 2009, 48, 973-977
13. Del Bene, J.; Yáñez, M.; Alkorta, I.; Elguero, J. An Ab Initio Study of the Structures and Selected Properties of 1,2-Dihydro-1,2- azaborine and Related Molecules J. Chem. Theory Comput. 2009, 5, 2239-2247
14. Fink, W.; Richards, J. Relative Aromaticity in Heteropolar Inorganic Analogs of Benzene J. Am. Chem. Soc. 1991, 113, 3393-3398
15. 6 J. Phys. Chem. A 1997, 101, 1409-1413
16. Schleyer, P.; Jiao, H.; Hommes, N.; Malkin, V.; Malkina, O. An Evaluation of the Aromaticity of Inorganic Rings: Refined Evidence from Magnetic Properties J. Am. Chem. Soc. 1997, 119, 12669-12670
17. Fernandez, I.; Frenking, G. Direct Estimate of Conjugation and Aromaticity in Cyclic Compounds With the EDA Method Faraday Discuss. 2007, 135, 403-421
18. Doerksen, R.; Thakkar, A. Azaborinines: Structures, Vibrational Frequencies, and Polarizabilities J. Phys. Chem. A 1998, 102, 4679-4686
19. Doerksen, R.; Thakkar, A. Structures, Vibrational Frequencies and Polarizabilities of Diazaborinines, Triazadiborinines, Azaboroles, and Oxazaboroles J. Phys. Chem. A 1999, 103, 2141-2151
20. Lamm, A.; Liu, S.-Y. How Stable Are 1,2-Dihydro-1,2-azaborines toward Water and Oxygen? Mol. Biosyst. 2009, 5, 1303 - 1305.
21. Tanjaroon, C.; Daly, A.; Marwitz, A.; Liu, S.-Y.; Kukolich, S. Microwave Measurements and Ab Initio Calculations of Structural and Electronic Properties of N -Ethyl-1,2-azaborine J. Chem. Phys. 2009, 131, 224312(1 - 9).
22. Chen, Z.; Wannere, C.; Corminboeuf, C.; Puchta, R.; Schleyer, P. Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion Chem. Rev. 2005, 105, 3842-3888 (Pubitemid 41630338)
23. Lazzeretti, P. Assessment of Aromaticity via Molecular Response Properties Phys. Chem. Chem. Phys. 2004, 6, 217-223
24. Klod, S.; Kleinpeter, E. Ab Initio Calculation of the Anisotropy Effect of Multiple Bonds and the Ring Current Effect of Arenes - Application in Conformational and Configurational Analysis J. Chem. Soc., Perkin Trans. 2 2001, 1893-1898
25. Kleinpeter, E.; Klod, S.; Koch, A. Visualization of Through Space NMR Shieldings of Aromatic and Anti-aromatic Molecules and a Simple Means to Compare and Estimate Aromaticity J. Mol. Struct.: THEOCHEM 2007, 811, 45-60
26. Lazzeretti, P. Ring Currents Prog. Nucl. Magn. Reson. Spectrosc. 2000, 36, 1-88
27. Fowler, P.; Steiner, E.; Havenith, R.; Jenneskens, J. Current Density, Chemical Shifts, and Aromaticity Magn. Reson. Chem. 2004, 42, 568-578
28. Soncini, A.; Fowler, P. W.; Lazzeretti, P.; Zanasi, R. Ring-Current Signatures in Shielding-Density Maps Chem. Phys. Lett. 2005, 401, 164-169
29. Pelloni, S.; Faglioni, F.; Zanasi, R.; Lazzeretti, P. Topology of Magnetic-Field-Induced Current-Density Field in Diatropic Monocyclic Molecules Phys. Rev. A 2006, 74, 012506(1-8).
30. Pelloni, S.; Lazzeretti, P.; Zanasi, R. Assessment of σ-Diatropicity of the Cyclopropane Molecule J. Phys. Chem. A 2007, 111, 8163-8169
31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.;, Gaussian 03, revision C.02, Gaussian, Inc.: Wallingford, CT, 2004.
32. Lazzeretti, P.; Malagoli, M.; Zanasi, R. Technical Report on Project Sistemi Informatici e Calcolo Parallelo; Research Report 1/67, CNR, 1991.
33. Keith, T. A.; Bader, R. F. W. Calculation of Magnetic Response Properties Using a Continuous Set of Gauge Transformations Chem. Phys. Lett. 1993, 210, 223-231
34. Zanasi, R. Coupled Hartree-Fock Calculations of Molecular Magnetic Properties Annihilating the Transverse-Paramagnetic Current Density J. Chem. Phys. 1996, 105, 1460-1469
35. Paraview 3.4.0; Sandia Corporation/Kitware Inc.: Albuquerque, MN/Clifton Park, NY, 2005-2008.
36. Schleyer, P.; Jiao, H. What is Aromaticity? Pure Appl. Chem. 1996, 68, 209 - 218.