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Volumn 112, Issue 1, 2008, Pages 125-133

Dimers of boroglycine and methylamine boronic acid: A computational comparison of the relative importance of dative versus hydrogen bonding

Author keywords

[No Author keywords available]

Indexed keywords

METHYLAMINE BORONIC ACID; PHARMACOLOGY;

EID: 38649134451     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp076537h     Document Type: Article
Times cited : (18)

References (125)
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    • 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.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Naskajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Parkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. G.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian03, revision B.02; Gaussian Inc.: Wallingford, CT, 2003.
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    • 2 dimer at the same computational levels.
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    • These SCRF PCM PBE1PBE/6-311++G(d,p) calculations often proved problematical: in some cases the calculations failed unless the additional spheres added to smooth the surface representing the solvent-solute boundary were removed; in other cases, the calculations converged to structures that were transition states with low imaginary frequencies (∼10 cm-1) and repeated attempts to locate the corresponding local minima were unsuccessful. Typically, conformers with one or two B:N dative bonds, e.g, 5a, 5b, 6, and 9a, were stable at this level, whereas conformers with one or two O-H⋯O hydrogen bonds but no B:N dative bond, e.g, 1, 3, and 7, were transition states; the doubly oxygen-bridged conformers 2 and 8 were also transition states
    • -1) and repeated attempts to locate the corresponding local minima were unsuccessful. Typically, conformers with one or two B:N dative bonds, e.g., 5a, 5b, 6, and 9a, were stable at this level, whereas conformers with one or two O-H⋯O hydrogen bonds but no B:N dative bond, e.g., 1, 3, and 7, were transition states; the doubly oxygen-bridged conformers 2 and 8 were also transition states.


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