A computational investigation of the nitrogen-boron interaction in o-(N, N-dialkylaminomethyl)arylboronate systems

Journal of Physical Chemistry A

Volumn 114, Issue 47, 2010, Pages 12531-12539

  Larkin, Joseph D ^a   Fossey, John S ^b   James, Tony D ^c   Brooks, Bernard R ^a   Bock, Charles W ^d,e  

^a NATIONAL HEART LUNG AND BLOOD INSTITUTE   (United States)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^c University of Bath   (United Kingdom)

^d THOMAS JEFFERSON UNIVERSITY   (United States)

^e FOX CHASE CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS ENVIRONMENT; ARYLBORONATES; BORON INTERACTION; C-PCM SOLVATION MODEL; COMPUTATIONAL INVESTIGATION; FIVE-MEMBERED RINGS; FREE ACIDS; GEOMETRY OPTIMIZATION; INSERTION REACTIONS; INTERMOLECULAR HYDROGEN; INTRAMOLECULAR HYDROGEN; PERTURBATION THEORY; RING STRUCTURES; SECOND ORDERS; SENSOR DEVELOPMENT; SEVEN-MEMBERED RINGS; SINGLE-POINT CALCULATIONS;

ACIDS; BORON; BORON COMPOUNDS; ESTERIFICATION; ESTERS; HYDROGEN; PERTURBATION TECHNIQUES;

DENSITY FUNCTIONAL THEORY;

BORON; CARBOHYDRATE; NITROGEN; SOLVENT; WATER;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER PROGRAM; COMPUTER SIMULATION; CONFORMATION; HYDROGEN BOND; METHODOLOGY; PHYSICAL CHEMISTRY; QUANTUM THEORY; THERMODYNAMICS;

BORON; CARBOHYDRATES; CHEMISTRY, PHYSICAL; COMPUTER SIMULATION; HYDROGEN BONDING; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NITROGEN; QUANTUM THEORY; SOFTWARE; SOLVENTS; THERMODYNAMICS; WATER;

EID: 78649563560     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp1087674     Document Type: Article

References (50)

1. Nakayama, J.; Ishii, A. Chemistry of dithiiranes, 1,2-dithietanes, and 1,2-dithietes. In Advances in Heterocyclic Chemistry; Academic Press: New York, 2000; Vol. 77; pp 221.
2. Mloston, G.; Majchrzak, A.; Senning, A.; Sotofte, I. J. Org. Chem. 2002, 67, 5690
3. Schreiner, P. R.; Reisenauer, H. P.; Romanski, J.; Mloston, G. J. Am. Chem. Soc. 2010, 132, 7240
4. Jakubowski, H. FASEB J. 1999, 13, 2277
5. Jakubowski, H. J. Nutr. 2000, 130, 377
6. Jakubowski, H. J. Biol. Chem. 1997, 272, 1935
7. Rowe, D. J. Perfum. Flavor. 1998, 23
8. Roling, I.; Schmarr, H.-G.; Eisenreich, W.; Engel, K.-H. J. Agric. Food Chem. 1998, 46, 668
9. Paryzek, Z.; Skiera, I. Org. Prep. Proc. Int. 2007, 39, 203
10. Holmberg, B.; Schjanberg, E. Arkiu Kemi. Mineral. Geol. 1940, 14A, 22
11. Schjånberg, E. Ber. Deutsch. Chem. Ges. 1941, 74, 1751
12. Fries, K.; Mengel, H. Ber. Deutsch. Chem. Ges. 1912, 45, 3408
13. Knunyants, I. L.; Linkova, M. G.; Kuleshova, N. D. Izv. Acad. Nauk SSSR, Ser. Khim. 1964, 644
14. Overberger, C. G.; Weise, J. K. J. Am. Chem. Soc. 1968, 90, 3533
15. Houk, K. N.; Jabbari, A.; Hall, H. K.; Aleman, C. J. Org. Chem. 2008, 73, 2674
16. Coulembier, O.; Degée, P.; Hedrick, J. L.; Dubois, P. Prog. Polym. Sci. 2006, 31, 723
17. Dugarte, N. Y.; Erben, M. F.; Romano, R. M.; Boese, R.; Ge, M.-F.; Li, Y.; Della Védova, C. O. J. Phys. Chem. A 2009, 113, 3662
18. Dugarte, N. Y.; Erben, M. F.; Romano, R. M.; Ge, M.-F.; Li, Y.; Della Védova, C. O. J. Phys. Chem. A 2010, 114, 9462
19. Bhar, D.; Chandrasekaran, S. Tetrahedron 1997, 53, 11835
20. Geronés, M.; Downs, A. J.; Erben, M. F.; Ge, M.; Romano, R. M.; Yao, L.; Della Védova, C. O. J. Phys. Chem. A 2008, 112, 5947
21. Wang, W.; Yao, L.; Zeng, X.; Ge, M.; Sun, Z.; Wang, D.; Ding, Y. J. Chem. Phys. 2006, 125, 234303
22. Wang, W.; Ge, M.; Yao, L.; Zeng, X.; Sun, Z.; Wang, D. ChemPhysChem 2006, 7, 1382-1387
23. Boese, R.; Nussbaumer, M. In situ crystallisation techniques. In Organic Crystal Chemistry; Jones, D. W., Ed.; Oxford University Press: Oxford, 1994; Vol. 7; pp 20.
24. Siemens. SHELTX-Plus Version SGI IRIS Indigo, a Complex Software Package for Solving, Refining and Displaying Crystal Strucutres; 1991.
25. 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.; Nakajima, 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.; Farkas, 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. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03; Revision B.04 ed.; Gaussian, Inc.: Pittsburgh PA, 2003.
26. Cederbaum, L. S.; Domcke, W. Adv. Chem. Phys. 1977, 36, 205
27. Cederbaum, L. S.; Schirmer, J.; Domcke, W.; von Niessen, W. J. Phys. B 1977, 10, L549
28. Zhao, M.; Gimarc, B. M. J. Phys. Chem. 1993, 97, 4023
29. Alemán, C.; Betran, O.; Casanovas, J.; Houk, K. N.; Hall, H. K. J. Org. Chem. 2009, 74, 6237
30. Fatheree, D. M.; Deeg, G. L.; Matthews, D. B.; Russell, J. G. Org. Magn. Res. 1982, 18, 92
31. Della Védova, C. O.; Romano, R. M.; Oberhammer, H. J. Org. Chem. 2004, 69, 5395
32. Ang, H. G.; Klapdor, M. F.; Kwik, W. L.; Lee, Y. W.; Mack, H. G.; Mootz, D.; Poll, W.; Oberhammer, H. J. Am. Chem. Soc. 1993, 115, 6929
33. Vujasinovic, I.; Veljkovic, J.; Mlinaric-Majerski, K.; Molcanov, K.; Kojic-Prodic, B. Tetrahedron 2006, 62, 2868
34. Philip, T.; Cook, R. L.; Malloy, T. B., Jr.; Allinger, N. L.; Chang, S.; Yuh, Y. J. Am. Chem. Soc. 1981, 103, 2151
35. Allinger, N. L.; Chang, S. H. M. Tetrahedron 1977, 33, 1561
36. Bach, R. D.; Dmitrenko, O. J. Am. Chem. Soc. 2006, 128, 4598
37. Saiyasombat, W.; Molloy, R.; Nicholson, T. M.; Johnson, A. F.; Ward, I. M.; Poshyachinda, S. Polymer 1998, 39, 5581
38. Kenneth, B. W. Angew. Chem., Int. Ed. 1986, 25, 312
39. Ringer, A. L.; Magers, D. H. J. Org. Chem. 2007, 72, 2533
40. Borst, M. L. G.; Ehlers, A. W.; Lammertsma, K. J. Org. Chem. 2005, 70, 8110
41. Kuz'yants, G. M. J. Struct. Chem. 1975, 696
42. Chua, Y. T.; Mok, C. Y.; Huang, H. H.; Novak, I.; Ng, S. C. J. Chem. Soc., Perkin Trans. 1996, 2, 577
43. Geronés, M.; Downs, A. J.; Erben, M. F.; Ge, M.; Romano, R. M.; Yao, L.; Della Védova, C. O. J. Phys. Chem. A 2008, 112, 5947
44. Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335
45. Erben, M. F.; Della Védova, C. O. Inorg. Chem. 2002, 41, 3740
46. Geronés, M.; Erben, M. F.; Romano, R. M.; Della Védova, C. O.; Yao, L.; Ge, M. J. Phys. Chem. A 2008, 112, 2228
47. Erben, M. F.; Della Védova, C. O.; Romano, R. M.; Boese, R.; Oberhammer, H.; Willner, H.; Sala, O. Inorg. Chem. 2002, 41, 1064
48. Fausto, R. J. Mol. Struct.: THEOCHEM 1994, 315, 123
49. Chin, W. S.; Xu, Z. P.; Mok, C. Y.; Huang, H. H.; Mutoh, H.; Masuda, S. J. Electron Spectrosc. Relat. Phenom. 1998, 97, 88-91
50. Isaksson, R.; Liljefors, T. J. Chem. Soc., Perkin Trans. 1980, 2, 1815