The stabilizing role of the intramolecular C-H⋯O hydrogen bond in cyclic amides derived from α-methylbenzylamine

Journal of Organic Chemistry

Volumn 80, Issue 9, 2015, Pages 4481-4490

  Sandoval Lira, Jacinto ^a   Fuentes, Lilia ^a   Quintero, Leticia ^a   Höpfl, Herbert ^b   Hernández Pérez, Julio M ^a   Terán, Joel L ^a   Sartillo Piscil, Fernando ^a  

^a BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^b CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; ATOMS;

CARBONYL GROUPS; CHIRAL AUXILIARIES; DFT CALCULATION; HYDROGEN ATOMS; HYDROGEN BONDING INTERACTIONS; METHYLBENZYLAMINE; SPATIAL ARRANGEMENTS; STABILIZING INTERACTIONS;

HYDROGEN BONDS;

ALPHA METHYLBENZYLAMINE; AMIDE; LACTAM DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION;

EID: 84928914525     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00286     Document Type: Article

References (54)

1. Sheiner, S. Hydrogen Bonding: A Theoretical Perspective; Oxford University Press: New York, 1997.
2. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991.
3. Donohue, J. In Structural Chemistry and Molecular Biology; Rich, A., Davidson, N., Eds.; W. H. Freeman: San Francisco, CA, 1968; pp 459-463.
4. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76
5. Steiner, T. J. Phys. Chem. A 2000, 104, 433-435
6. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.
7. Desiraju, G. R. Science 1997, 278, 404-405
8. Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449
9. Mottamalm, M.; Lazaridis, T. Biochemistry 2005, 44, 1607-1613
10. Castellano, R. K. Curr. Org. Chem. 2004, 8, 845-865
11. Yohannan, S.; Faham, S.; Yang, D.; Grosfeld, D.; Chamberlain, A. K.; Bowie, J. U. J. Am. Chem. Soc. 2004, 126, 2284-2285
12. Chamberlain, A. K.; Bowie, J. U. J. Mol. Bol. 2002, 322, 497-503
13. Vargas, R.; Garza, J.; Dixon, D. A.; Hay, B. P. J. Am. Chem. Soc. 2000, 122, 4750-4755
14. Nagawa, Y.; Yamagaki, T.; Nakanishi, H. Tetrahedron Lett. 1998, 39, 1393-1396
15. Seiler, P.; Weisman, R.; Glendening, E. D.; Weinhold, F.; Johnson, V. B.; Dunitz, J. D. Angew. Chem., Int. Ed. Engl. 1987, 26, 1175-1177
16. Parthasarathi, R.; Subramanian, V.; Sathyamurthy, N. J. Phys. Chem. A 2006, 110, 3349-3351
17. Scheiner, S.; Kar, T.; Gu, Y. J. Biol. Chem. 2001, 276, 9832-9837
18. Corey, E. J.; Rohde, J. J. Tetrahedron Lett. 1997, 38, 37-40
19. Corey, E. J.; Rohde, J. J.; Fischer, A.; Azimioara, M. D. Tetrahedron Lett. 1997, 38, 33-36
20. Jones, C. R.; Baruah, P. K.; Thompson, A. L.; Scheiner, S.; Smith, M. D. J. Am. Chem. Soc. 2012, 134, 12064-12071
21. Rodríguez-Soria, V.; Sánchez, M.; Quintero, L.; Sartillo-Piscil, F. Tetrahedron 2004, 60, 10809-10815
22. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663-2676
23. Juaristi, E.; Escalante, J.; León-Romo, J. L.; Reyes, A. Tetrahedron: Asymmetry 1998, 9, 715-740
24. Rodríguez-Soria, V.; Quintero, L.; Sartillo-Piscil, F. Tetrahedron 2008, 64, 2750-2754
25. Rodríguez-Soria, V.; Quintero, L.; Sartillo-Piscil, F. Tetrahedron Lett. 2007, 48, 4305-4308
26. Sandoval-Lira, J.; Hernández-Pérez, J. M.; Sartillo-Piscil, F. Tetrahedron Lett. 2012, 53, 6689-6693
27. Fuentes, L.; Quintero, L.; Cordero-Vargas; Eustaquio, C.; Terán, J. L.; Sartillo-Piscil, F. Tetrahedron Lett. 2011, 52, 3630-3632
28. Becke, A. D. J. Chem. Phys. 1993, 98, 1372
29. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
30. Hehre, W. J.; Ditchfeld, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257
31. London, F. Z. Phys. 1930, 63, 245-279
32. Kruse, H.; Goerigk, L.; Grimme, S. J. Org. Chem. 2012, 77, 10824-10834
33. Goerigk, L.; Reimers, J. R. J. Chem. Theory Comput. 2013, 9, 3240-3251
34. Lodewyk, M. W.; Siebert, M. R.; Tantillo, D. J. Chem. Rev. 2012, 112, 1839-1862
35. Keith, T. A. AIMAll (version 12.05.09); TK Gristmill Software: Overland Park, KS, 2012; aim.tkgristmill.com.
36. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford, CT, 2009.
37. Bader, R. F. W. Atoms in Molecules, A Quantum Theory; Oxford University Press: Oxford, 1990.
38. Kemnitz, C. R.; Loewen, M. J. J, Am. Chem. Soc. 2007, 129, 2521-2528
39. Mujika, J. I.; Matxain, J. M.; Eriksson, L. A.; Lopez, X. Chem.-Eur. J. 2006, 12, 7215-7224
40. Fuentes, L.; Osorio, U.; Quintero, L.; Höpfl, H.; Vázquez-Cabrera, N.; Sartillo-Piscil, F. J. Org. Chem. 2012, 77, 5515-5524
41. CCDC 1038283 (11). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
42. CCDC 1038284 (12). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
43. Zárate, A.; Orea, L.; Juárez, J. R.; Castro, A.; Mendoza, A.; Gnecco, D.; Terán, J. L. Synth. Commun. 2014, 44, 2838-2847
44. Koch, U.; P. L. A. Popelier, P. L. A. J. Phys. Chem. 1995, 99, 9747-9754
45. Aparicio, D. M.; Terán, J. L.; Roa, L. F.; Gnecco, D.; Juárez, J. R.; Orea, M. L.; Mendoza, A.; Flores-Alamo, M.; Micouin, L. Synthesis 2011, 14, 2310-2320
46. Fuentes, L.; Hernández-Juárez, M.; Terán, J. L.; Quintero, L.; Sartillo-Piscil, F. Synlett. 2013, 24, 878-882
47. Juárez-Calderón, M.; Aparicio, D. M.; Gnecco, D.; Juárez, J. R.; Orea, L.; Mendoza, A.; Sartillo-Piscil, F.; del Olmo, E.; Terán, J. L. Tetrahedron Lett. 2013, 54, 2729-2732
48. Allinger, N. L.; Hirsch, J. A.; Miller, M. A.; Tyminski, I. J. J. Am. Chem. Soc. 1968, 90, 5773-5780
49. Witosinska, A.; Musielak, B.; Serda, P.; Owinska, M.; Rys, B. J. Org. Chem. 2012, 77, 9784-9794
50. Hobza, P.; Havlas, Z. Chem. Rev. 2000, 100, 4253-4264
51. Joseph, J.; Jemmis, E. D. J. Am. Chem. Soc. 2007, 129, 4620-4632
52. Staszewska-Krajewska, O.; Bocian, W.; Maciejko, M.; Szczesnik, P.; Szymczak, K.; Chmielewski, M.; Furman, B. Arkivok 2014, iii, 143-153
53. Stewart, W. E.; Siddall, T. H. Chem. Rev. 1970, 70, 517-551
54. Palillero, A.; Terán, J. L.; Gnecco, D.; Juárez, J. R.; Orea, M. L.; Castro, A. Tetrahedron Lett. 2009, 50, 4208-4211