Concomitant polymorphism of a pyridine-2,6-dicarboxamide derivative in a single space group: Experimental and molecular modeling study

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Volumn 86, Issue , 2012, Pages 614-624

  Özdemir, Namik ^a   Dayan, Osman ^b   Çetinkaya, Bekir ^c   Akgül, Cahit ^b  

^a ONDOKUZ MAYIS UNIVERSITY   (Turkey)

^b ÇANAKKALE ONSEKIZ MART UNIVERSITY   (Turkey)

^c EGE UNIVERSITY   (Turkey)

Author keywords

Crystal structure; Density functional theory method (DFT); Entropy enthalpy compensation; IR and NMR spectroscopy; Solvent effect; Transfer hydrogenation

Indexed keywords

DENSITY FUNCTIONAL THEORY METHOD (DFT); ENTROPY-ENTHALPY COMPENSATION; IR AND NMR SPECTROSCOPY; SOLVENT EFFECTS; TRANSFER HYDROGENATION;

BACTERIA; CATALYST ACTIVITY; CRYSTAL STRUCTURE; HYDROGEN BONDS; HYDROGENATION; KETONES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; PYRIDINE; QUANTUM CHEMISTRY; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL); THERMOANALYSIS; X RAY DIFFRACTION;

DENSITY FUNCTIONAL THEORY;

ANTIINFECTIVE AGENT; PYRIDINE 2,6 DICARBOXAMIDE; PYRIDINE DERIVATIVE; PYRIDINE-2,6-DICARBOXAMIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ELECTRICITY; ENTROPY; HYDROGEN BOND; INFRARED SPECTROSCOPY; NONLINEAR SYSTEM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM THEORY; SURFACE PROPERTY; SYNTHESIS; TEMPERATURE; VIBRATION; X RAY CRYSTALLOGRAPHY;

ANTI-BACTERIAL AGENTS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; ELECTRICITY; ENTROPY; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NONLINEAR DYNAMICS; PYRIDINES; QUANTUM THEORY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SURFACE PROPERTIES; TEMPERATURE; VIBRATION;

EID: 83655192945     PISSN: 13861425     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.saa.2011.11.026     Document Type: Article

References (78)

1. M.Y. Li, P.Z. Hu, W.R. Zhu, and K.X. Xu Chin. Chem. Lett. 14 2003 572 574
2. N.C. Singha, and D.N. Sathyanarayana J. Mol. Struct. 403 1997 123 135
3. A. Mishra, N.K. Kaushik, A.K. Verma, and R. Gupta Eur. J. Med. Chem. 43 2008 2189 2196
4. S.M. Redmore, C.E.F. Rickard, S.J. Webb, and L.J. Wright Inorg. Chem. 36 1997 4743 4748
5. T. Kawamoto, B.S. Hammes, R. Ostrander, A.L. Rheingold, and A.S. Borovik Inorg. Chem. 37 1998 3424 3427
6. K. Gudasi, R. Vadavi, R. Shenoy, M. Patil, S.A. Patil, and M. Nethaji Inorg. Chim. Acta 358 2005 3799 3806
7. R.-R. Tang, G.-L. Gu, and Q. Zhao Spectrochim. Acta A 71 2008 371 376
8. D.A. Conlon, and N. Yasuda Adv. Synth. Catal. 343 2001 137 138
9. B.M. Trost, and I. Hachiya J. Am. Chem. Soc. 120 1998 1104 1105
10. V.C. Gibson, C. Redshaw, and G.A. Solan Chem. Rev. 107 2007 1745 1776
11. X.-Y. Lu, H.-J. Xu, and X.-T. Chen Inorg. Chem. Commun. 12 2009 887 889
12. O. Dayan, and B. etinkaya J. Mol. Catal. A Chem. 271 2007 134 141
13. B. etinkaya, E. etinkaya, M. Brookhart, and P.S. White J. Mol. Catal. A Chem. 142 1999 101 112
14. S.R. Collinson, T. Gelbrick, M.B. Hursthouse, and J.H.R. Tucker Chem. Commun. 6 2001 555 556
15. I. Huc, M.J. Krische, D.P. Funeriu, and J.-M. Lehn Eur. J. Inorg. Chem. 9 1999 1415 1420
16. J.D. Epperson, L.-J. Ming, G.R. Baker, and G.R. Newkome J. Am. Chem. Soc. 123 2001 8583 8592
17. J. Zhang, Q. Liu, C. Duan, Y. Shao, J. Ding, Z. Miao, X.-Z. You, and Z.J. Guo J. Chem. Soc. Dalton Trans. 4 2002 591 597
18. S.L. Jain, P. Bhattacharyya, H.L. Milton, A.M.Z. Slawin, J.A. Crayston, and J.D. Woollins Dalton Trans. 6 2004 862 871
19. J.-M. Lehn Angew. Chem. Int. Ed. Engl. 29 1990 1304 1319
20. J.-M. Lehn Supramolecular Chemistry: Concept and Perspective 1995 VCH New York
21. Y. Aoyama V. Balzani, L. De Cola, Supramolecular Chemistry 1992 Kluwer Dordrecht 17
22. M. Suárez, J.-M. Lehn, S.C. Zimmerman, A. Skoulios, and B. Heinrich J. Am. Chem. Soc. 120 1998 9526 9532
23. J. Bernstein, M.C. Etter, and L. Leiserowitz H.B. Burgi, J.D. Dunitz, Structure Correlation vol. 2 1993 VCH Weinheim 431 507
24. G.R. Desiraju Crystal Engineering: The Design of Organic Solids 1989 Elsevier Amsterdam
25. J. Hulliger Angew. Chem. Int. Ed. Engl. 33 1994 143 162
26. S.J. Geib, C. Vincent, E. Fan, and A.D. Hamilton Angew. Chem. Int. Ed. Engl. 32 1993 119 121
27. Y. Hamuro, S.J. Geib, and A.D. Hamilton Angew. Chem. Int. Ed. Engl. 33 1994 446 448
28. T. Kawamoto, B.S. Hammes, B. Haggerty, G.P.A. Yap, A.L. Rheingold, and A.S. Borovik J. Am. Chem. Soc. 118 1996 285 286
29. Y. Hamuro, S.J. Geib, and A.D. Hamilton J. Am. Chem. Soc. 119 1997 10587 10593
30. Q. Yu, T.E. Baroni, L. Liable-Sands, A.L. Rheingold, and A.S. Borovik Tetrahedron Lett. 39 1998 6831 6834
31. J. Bernstein, R.J. Davey, and J.-O. Henck Angew. Chem. Int. Ed. Engl. 38 1999 3440 3461
32. J.D. Duntiz, and J. Bernstein Acc. Chem. Res. 28 1995 193 200
33. J. Bernstein, and J.-O. Henck Cryst. Eng. 1 1998 119 128
34. A. etin, and O. Dayan Chin. J. Chem. 27 2009 978 982
35. A.D. Cort, C. Pasquini, and L. Schiaffino Supramol. Chem. 19 2007 79 87
36. C. Akgül, and. Kaya Indian J. Biochem. Biophys. 41 2004 120 122
37. G.M. Sheldrick SHELXS-97, Program for the Solution of Crystal Structures 1997 University of Göttingen Germany
38. G.M. Sheldrick SHELXL-97, Program for Crystal Structures Refinement 1997 University of Göttingen Germany
39. Stoe, and Cie X-AREA Version 1.18 and X-RED32 Version 1.04 2002 Stoe & Cie Darmstadt, Germany
40. A.L. Spek Acta Crystallogr. A 64 2009 112 122
41. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
42. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
43. R. Ditchfield, W.J. Hehre, and J.A. Pople J. Chem. Phys. 54 1971 724 728
44. J.B. Foresman, and Æ. Frisch Exploring Chemistry with Electronic Structure Methods 2nd ed. 1996 Gaussian Inc. Pittsburgh, PA
45. R. Ditchfield J. Chem. Phys. 56 1972 5688 5691
46. K. Wolinski, J.F. Hinton, and P. Pulay J. Am. Chem. Soc. 112 1990 8251 8260
47. R. Dennington II, T. Keith, and J. Millam Gauss View, Version 4.1.2 2007 Semichem Inc. Shawnee Mission, KS
48. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision E.01 2004 Gaussian Inc. Wallingford, CT
49. E. Cancs, B. Mennucci, and J. Tomasi J. Chem. Phys. 107 1997 3032 3041
50. L. Onsager J. Am. Chem. Soc. 58 1936 1486 1493
51. F. Safinejad, C.D. Thompson, and M. Asghari-Khiavi J. Mol. Model. 15 2009 1119 1124
52. L.J. Farrugia J. Appl. Chem. 30 1997 565
53. A. Kovalchuk, J.L. Bricks, G. Reck, K. Rurack, B. Schulz, A. Szumna, and H. Weißhoff Chem. Commun. 17 2004 1946 1947
54. Q.Y. Yang, Z.Y. Zhou, and J.Y. Qi Acta Crystallogr. E 57 2001 o1161 o1162
55. C.J. Sumby, and L.R. Hanton Tetrahedron 65 2009 4681 4691
56. J.L. Bricks, G. Reck, K. Rurack, B. Schulz, and M. Spieles Supramol. Chem. 15 2003 189 197
57. J.Y. Qi, Q.Y. Yang, K.H. Lam, Z.Y. Zhou, and A.S.C. Chan Acta Crystallogr. E 59 2003 o415 o416
58. Z. Yin, Z. Li, W.-Z. Yang, J. He, and J.-P. Cheng Struct. Chem. 16 2005 641 647
59. A. Picot, C. Feuvrie, C. Barsu, F. Malvolti, B. Le Guennic, H. Le Bozec, C. Andraud, L. Toupet, and O. Maury Tetrahedron 64 2008 399 411
60. J.F. Malone, C.M. Murray, and G.M. Dolan Chem. Mater. 9 1997 2983 2989
61. J. Bernstein, R.E. Davis, L. Shimoni, and N.-L. Chang Angew. Chem. Int. Ed. Engl. 34 1995 1555 1573
62. P. Hobza, and R. Zahradnik Chem. Rev. 88 1988 871 897
63. F.B. van Duijneveldt, J.G.C.M. van Duijneveldt-van de Rijdt, and J.H. van Lenthe Chem. Rev. 94 1994 1873 1885
64. S.F. Boys, and F. Bernardi Mol. Phys. 19 1970 553 566
65. I. Fleming Frontier Orbitals and Organic Chemical Reactions 1976 Wiley London
66. Y.-X. Sun, Q.-L. Hao, W.-X. Wei, Z.-X. Yu, L.-D. Lu, X. Wang, and Y.-S. Wang J. Mol. Struct.: THEOCHEM. 904 2009 74 82
67. C. Andraud, T. Brotin, C. Garcia, F. Pellé, P. Goldner, B. Bigot, and A. Collet J. Am. Chem. Soc. 116 1994 2094 2102
68. V.M. Geskin, C. Lambert, and J.-L. Brédas J. Am. Chem. Soc. 125 2003 15651 15658
69. M. Nakano, H. Fujita, M. Takahata, and K. Yamaguchi J. Am. Chem. Soc. 124 2002 9648 9655
70. D. Sajan, H. Joe, V.S. Jayakumar, and J. Zaleski J. Mol. Struct. 785 2006 43 53
71. K.S. Thanthiriwatte, and K.M.N. de Silva J. Mol. Struct.: THEOCHEM. 617 2002 169 175
72. G.A. Babu, and P. Ramasamy Curr. Appl. Phys. 10 2010 214 220
73. H. Tanak J. Mol. Struct.: THEOCHEM. 950 2010 5 12
74. M. Yavuz, and H. Tanak J. Mol. Struct.: THEOCHEM. 961 2010 9 16
75. L. Liu, and Q.-X. Guo Chem. Rev. 101 2001 673 695
76. F.N. Hosseini Polyhedron 29 2010 349 353
77. D.H. Leung, R.G. Bergman, and K.N. Raymond J. Am. Chem. Soc. 130 2008 2798 2805
78. E.B. Starikov, and B. Nordén J. Phys. Chem. B 111 2007 14431 14435